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Influence of Protecting Groups on the Reactivity and Selectivity of Glycosylation: Chemistry of the 4,6-O-Benzylidene Protected Mannopyranosyl Donors and Related Species

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Reactivity Tuning in Oligosaccharide Assembly

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 301))

Abstract

The genesis and development of the 4,6-O-benzylidene acetal method for the preparation of β-mannopyranosides are reviewed. Particular emphasis is placed on the influence of the various protecting groups on stereoselectivity and these effects are interpreted in the framework of a general mechanistic scheme invoking a series of solvent-separated and contact ion pairs in dynamic equilibrium with a covalent α-glycosyl trifluoromethanesulfonate.

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References

  1. Fraser-Reid B (1975) Acc Chem Res 8:192

    CAS  Google Scholar 

  2. Barresi F, Hindsgaul O (1995) J Carbohydr Chem 14:1043

    CAS  Google Scholar 

  3. Zhu X, Schmidt RR (2009) Angew Chem Int Ed 48:1900

    CAS  Google Scholar 

  4. Gridley JJ, Osborn HMI (2000) J Chem Soc Perkin Trans 1:1471

    Google Scholar 

  5. Demchenko AV (2003) Curr Org Chem 7:35

    CAS  Google Scholar 

  6. Demchenko AV (2003) Synlett 1225

    Google Scholar 

  7. Barresi F, Hindsgaul O (1996) In: Khan SH, O’Neill RA (eds) Modern methods in carbohydrate synthesis. Harwood Academic Publishers, Amsterdam, p 251

    Google Scholar 

  8. Pozsgay V (2000) In: Ernst B, Hart GW, Sinaÿ P (eds) Carbohydrates in chemistry and biology, vol 1. Wiley-VCH, Weinheim, p 319

    Google Scholar 

  9. Ito Y, Ohnishi Y (2001) In: Fraser-Reid B, Kuniaki T, Thiem J (eds) Glycoscience: chemistry and chemical biology, vol 2. Springer-Verlag, Berlin, p 1589

    Google Scholar 

  10. Brunckova J, Crich D, Yao Q (1994) Tetrahedron Lett 35:6619

    CAS  Google Scholar 

  11. Crich D, Sun S, Brunckova J (1996) J Org Chem 61:605

    CAS  Google Scholar 

  12. Crich D, Hwang J-T, Yuan H (1996) J Org Chem 61:6189

    CAS  Google Scholar 

  13. Crich D, Sun S (1996) J Org Chem 61:4506

    CAS  Google Scholar 

  14. Crich D, Sun S (1997) J Org Chem 62:1198

    CAS  Google Scholar 

  15. Kahne D, Walker S, Cheng Y, Engen DV (1989) J Am Chem Soc 111:6881

    CAS  Google Scholar 

  16. Crich D, Smith M, Yao Q, Picione J (2001) Synthesis 323

    Google Scholar 

  17. Crich D, Li H (2002) J Org Chem 67:4640

    CAS  Google Scholar 

  18. Crich D, Sun S (1998) Tetrahedron 54:8321

    CAS  Google Scholar 

  19. Codée JDC, Kröck L, Castagner B, Seeberger PH (2008) Chem Eur J 14:3987

    Google Scholar 

  20. Crich D, Mataka J, Zakharov LN, Rheingold AL, Wink DJ (2002) J Am Chem Soc 124:6028

    CAS  Google Scholar 

  21. Crich D, Lim LBL (2004) Org React 64:115

    CAS  Google Scholar 

  22. Ferrieres V, Joutel J, Boulch R, Roussel M, Toupet L, Plusquellec D (2000) Tetrahedron Lett 41:5515

    CAS  Google Scholar 

  23. Nukada T, Bérces A, Wang L, Zgierski MZ, Whitfield DM (2005) Carbohydr Res 340:841

    CAS  Google Scholar 

  24. Nukada T, Berces A, Whitfield DM (2002) Carbohydr Res 337:765

    CAS  Google Scholar 

  25. Whitfield DM (2009) Adv Carbohydr Chem Biochem 62:83

    CAS  Google Scholar 

  26. Stevens RV (1984) Acc Chem Res 17:289

    CAS  Google Scholar 

  27. Kirby AJ (1983) The anomeric effect and related stereoelectronic effects at oxygen. Springer-Verlag, Berlin

    Google Scholar 

  28. Deslongchamps P (1983) Stereoelectronic effects in organic chemistry. Pergamon, Oxford

    Google Scholar 

  29. Crich D, Sun S (1997) J Am Chem Soc 119:11217

    CAS  Google Scholar 

  30. Crich D, Sun S (1998) J Am Chem Soc 120:435

    CAS  Google Scholar 

  31. Huang X, Huang L, Wang H, Ye X-S (2004) Angew Chem Int Ed 43:5221

    CAS  Google Scholar 

  32. Crich D, Cai F, Yang F (2008) Carbohydr Res 343:1858

    CAS  Google Scholar 

  33. Morishita T, Furukawa N, Oae S (1981) Tetrahedron 37:3115

    CAS  Google Scholar 

  34. Crich D, Smith M (2000) Org Lett 2:4067

    CAS  Google Scholar 

  35. Crich D, Smith M (2001) J Am Chem Soc 123:9015

    CAS  Google Scholar 

  36. Codée JDC, van den Bos LJ, Litjens REJN, Overkleeft HS, van Boeckel CAA, van Boom JH, van der Marel GA (2004) Tetrahedron 60:1057

    Google Scholar 

  37. Crich D, Banerjee A, Li W, Yao Q (2005) J Carbohydr Chem 24:415

    CAS  Google Scholar 

  38. Wang C, Wang H, Huang X, Zhang L-H, Ye X-S (2006) Synlett 2846

    Google Scholar 

  39. Durón SG, Polat T, Wong C-H (2004) Org Lett 6:839

    Google Scholar 

  40. Tatai J, Fügedi P (2007) Org Lett 9:4647

    CAS  Google Scholar 

  41. Nokami T, Shibuya A, Tsuyama H, Suga S, Bowers AA, Crich D, Yoshida J-i (2007) J Am Chem Soc 129:10922

    CAS  Google Scholar 

  42. Crich D, Li L (2007) J Org Chem 72:1681

    CAS  Google Scholar 

  43. Crich D, Pedersen CM, Bowers AA, Wink DJ (2007) J Org Chem 72:1553

    CAS  Google Scholar 

  44. Crich D, Cai W (1999) J Org Chem 64:4926

    CAS  Google Scholar 

  45. Crich D, Cai W, Dai Z (2000) J Org Chem 65:1291

    CAS  Google Scholar 

  46. Crich D, Vinogradova O (2007) J Am Chem Soc 129:11756

    CAS  Google Scholar 

  47. Crich D, Jayalath P (2005) J Org Chem 70:7252

    CAS  Google Scholar 

  48. Crich D, Subramanian V, Hutton TK (2007) Tetrahedron 63:5042

    CAS  Google Scholar 

  49. Crich D, Bowers AA (2006) J Org Chem 71:3452

    CAS  Google Scholar 

  50. Crich D, Hutton TK, Banerjee A, Jayalath P, Picione J (2005) Tetrahedron: Asymmetry 16:105

    CAS  Google Scholar 

  51. Crich D, Vinogradova O (2006) J Org Chem 71:8473

    CAS  Google Scholar 

  52. Pavia AA, Rocheville JM, Ung SN (1980) Carbohydr Res 79:79

    CAS  Google Scholar 

  53. Lacombe JM, Pavia AA, Rocheville JM (1981) Can J Chem 59:473

    CAS  Google Scholar 

  54. Pavia AA, Ung-Chhun SN (1981) Can J Chem 59:482

    CAS  Google Scholar 

  55. Leroux J, Perlin AS (1978) Carbohydr Res 67:163

    CAS  Google Scholar 

  56. Leroux J, Perlin AS (1976) Carbohydr Res 47:C8

    CAS  Google Scholar 

  57. Kronzer FJ, Schuerch C (1973) Carbohydr Res 27:379

    CAS  Google Scholar 

  58. Lucas TJ, Schuerch C (1975) Carbohydr Res 39:39

    CAS  Google Scholar 

  59. Marousek V, Lucas TJ, Wheat PE, Schuerch C (1978) Carbohydr Res 60:85

    CAS  Google Scholar 

  60. Srivastava VK, Schuerch C (1980) Carbohydr Res 79:C13

    CAS  Google Scholar 

  61. Srivastava VK, Schuerch C (1981) J Org Chem 46:1121

    CAS  Google Scholar 

  62. Garcia BA, Gin DY (2000) J Am Chem Soc 122:4269

    CAS  Google Scholar 

  63. Crich D, Chandrasekera NS (2004) Angew Chem Int Ed 43:5386

    CAS  Google Scholar 

  64. Singleton DA, Thomas AA (1995) J Am Chem Soc 117:9357

    CAS  Google Scholar 

  65. Westaway KC (2006) Adv Phys Org Chem 41:217

    CAS  Google Scholar 

  66. Peters KS (2007) Chem Rev 107:859

    CAS  Google Scholar 

  67. Horenstein NA (2006) Adv Phys Org Chem 41:275

    CAS  Google Scholar 

  68. El-Badri MH, Willenbring D, Tantillo DJ, Gervay-Hague J (2007) J Org Chem 72:4663

    CAS  Google Scholar 

  69. Amyes TL, Jencks WP (1989) J Am Chem Soc 111:7888

    CAS  Google Scholar 

  70. Zechel DL, Withers SG (2000) Acc Chem Res 33:11

    CAS  Google Scholar 

  71. Bohé L, Crich D (2011) CR Chimie 14: in press

    Google Scholar 

  72. Matsumoto K, Ueoka K, Suzuki S, Suga S, Yoshida J-i (2009) Tetrahedron 65:10901

    CAS  Google Scholar 

  73. Winstein S, Clippinger E, Fainberg AH, Heck R, Robinson GC (1956) J Am Chem Soc 78:328

    CAS  Google Scholar 

  74. Richard JP, Amyes Tl, Toteva MM, Tsuji Y (2004) Adv Phys Org Chem 39:1

    CAS  Google Scholar 

  75. Rhind-Tutt AJ, Vernon CA (1960) J Chem Soc 4637

    Google Scholar 

  76. Lemieux RU, Hendriks KB, Stick RV, James K (1975) J Am Chem Soc 97:4056

    CAS  Google Scholar 

  77. Zeng Y, Wang Z, Whitfield D, Huang X (2008) J Org Chem 73:7952

    CAS  Google Scholar 

  78. Walvoort MTC, Lodder G, Mazurek J, Overkleeft HS, Codée JDC, van der Marel GA (2009) J Am Chem Soc 131:12080

    CAS  Google Scholar 

  79. Hoffmann R, Minkin VI, Carpenter BK (1996) Bull Soc Chim Fr 133:117

    CAS  Google Scholar 

  80. Crich D, Dudkin V (2000) Org Lett 2:3941

    CAS  Google Scholar 

  81. Crich D, Dudkin V (2002) J Am Chem Soc 124:2263

    CAS  Google Scholar 

  82. Fraser-Reid B, Wu ZC, Andrews W, Skowronski E (1991) J Am Chem Soc 113:1434

    CAS  Google Scholar 

  83. Andrews CW, Rodebaugh R, Fraser-Reid B (1996) J Org Chem 61:5280

    CAS  Google Scholar 

  84. Jensen HH, Nordstrom M, Bols M (2004) J Am Chem Soc 126:9205

    CAS  Google Scholar 

  85. Bock K, Duus JO (1994) J Carbohydr Chem 13:513

    CAS  Google Scholar 

  86. Crich D, Banerjee A (2006) J Am Chem Soc 128:8078

    CAS  Google Scholar 

  87. Reich HJ, Dykstra RR (1993) J Am Chem Soc 115:7041

    CAS  Google Scholar 

  88. Crich D, Smith M (2002) J Am Chem Soc 124:8867

    CAS  Google Scholar 

  89. Crich D, Yao Q (2004) J Am Chem Soc 126:8232

    CAS  Google Scholar 

  90. Ley SV, Baeschlin DK, Dixon DJ, Foster AC, Ince SJ, Priepke HWM, Reynolds DJ (2001) Chem Rev 101:53

    CAS  Google Scholar 

  91. Thompson HW, Gaglani KD (1993) J Chem Soc Perkin Trans 2:967

    Google Scholar 

  92. Olsson JDM, Landstroem J, Roennols J, Oscarson S, Widmalm G (2009) Org Biomol Chem 7:162

    Google Scholar 

  93. Kajimoto T, Ishioka Y, Katoh T, Node M (2006) Bioorg Med Chem Lett 16:5736

    CAS  Google Scholar 

  94. Hanashima S, Inamori K-i, Manabe S, Taniguchi N, Ito Y (2006) Chem Eur J 12:3449

    CAS  Google Scholar 

  95. El Alaoui A, Schmidt F, Monneret C, Florent J-C (2006) J Org Chem 71:9628

    CAS  Google Scholar 

  96. Chevalier R, Esnault J, Vandewalle P, Sendid B, Colombel J-F, Poulain D, Mallet JM (2006) Tetrahedron 61:7669

    Google Scholar 

  97. Crich D, Dai Z, Gastaldi S (1999) J Org Chem 64:5224

    CAS  Google Scholar 

  98. Crich D, Barba GR (1998) Tetrahedron Lett 39:9339

    CAS  Google Scholar 

  99. Crich D, de la Mora MA, Cruz R (2002) Tetrahedron 58:35

    CAS  Google Scholar 

  100. Crich D, Jayalath P, Hutton TK (2006) J Org Chem 71:3064

    CAS  Google Scholar 

  101. Crich D, Karatholuvhu MS (2008) J Org Chem 73:5173

    CAS  Google Scholar 

  102. Crich D, Wu B (2006) Org Lett 8:4879

    CAS  Google Scholar 

  103. Dromer F, Chevalier R, Sendid B, Improvisi L, Jouault T, Robert R, Mallet JM, Poulain D (2002) Antimicrob Agents Chemother 46:3869

    CAS  Google Scholar 

  104. Bedini E, Carabellese A, Barone G, Parrilli M (2005) J Org Chem 70:8064

    CAS  Google Scholar 

  105. Gorin PAJ, Perlin AS (1961) Can J Chem 39:2474

    CAS  Google Scholar 

  106. Crich D, Vinod AU, Picione J (2003) J Org Chem 68:8453

    CAS  Google Scholar 

  107. Backinowskii LV, Balan NF, Shashkov AS, Kochetkov NK (1980) Carbohydr Res 84:225

    Google Scholar 

  108. Crich D, Vinod AU, Picione J, Wink DJ (2005) ARKIVOC vi:339

    Google Scholar 

  109. Manabe S, Ishii K, Hashizume D, Ito Y (2007) Acta Crystallogr E63:o3028

    Google Scholar 

  110. Baek JY, Lee B-Y, Jo MG, Kim KS (2009) J Am Chem Soc 131:17705

    CAS  Google Scholar 

  111. Crich D, Hu T, Cai F (2008) J Org Chem 73:8942

    CAS  Google Scholar 

  112. Gonzalez-Outeiriño J (2005) J Org Chem 70:2486

    Google Scholar 

  113. Schweitzer WB, Dunitz JD (1982) Helv Chim Acta 65:1547

    Google Scholar 

  114. Crich D, Picione J (2003) Org Lett 5:781

    CAS  Google Scholar 

  115. De Meo C, Kamat MN, Demchenko AV (2005) Eur J Org Chem 706

    Google Scholar 

  116. van Boeckel CAA, Beetz T, van Aelst SF (1984) Tetrahedron 40:4097

    Google Scholar 

  117. Tanaka H, Yoshizawa A, Takahashi T (2007) Angew Chem Int Ed 46:2505

    CAS  Google Scholar 

  118. Crich D, Dudkin V (2000) Tetrahedron Lett 41:5643

    CAS  Google Scholar 

  119. Crich D, Li W, Li H (2004) J Am Chem Soc 126:15081

    CAS  Google Scholar 

  120. Crich D, Wu B, Jayalath P (2007) J Org Chem 72:6806

    CAS  Google Scholar 

  121. Crich D (2007) In: Demchenko AV (ed) ACS symposium series, vol 960. American Chemical Society, Washington, p 60

    Google Scholar 

  122. Schneider H-J, Hoppen V (1978) J Org Chem 43:3866

    CAS  Google Scholar 

  123. Sülze D, Gatial A, Karlsson A, Klaeboe P, Nielsen CJ (1988) J Mol Struct 174:207

    Google Scholar 

  124. Jensen FR, Bushweller CH, Beck BH (1969) J Am Chem Soc 91:344

    CAS  Google Scholar 

  125. Bugay DE, Bushweller CH, Danehy CT, Hoogasian S, Blersch JA, Leenstra WR (1989) J Phys Chem 93:3908

    CAS  Google Scholar 

  126. Subbotin OA, Sergeyev NM (1975) J Am Chem Soc 97:1080

    CAS  Google Scholar 

  127. Chu P-S, True NS (1985) J Phys Chem 89:5613

    CAS  Google Scholar 

  128. Jensen FR, Bushweller CH (1971) Adv Alicycl Chem 3:139

    CAS  Google Scholar 

  129. Crich D, Li L, Shirai M (2009) J Org Chem 74:2486

    CAS  Google Scholar 

  130. Crich D, Xu H (2007) J Org Chem 72:5183

    CAS  Google Scholar 

  131. Crich D, Li L (2009) J Org Chem 74:773

    CAS  Google Scholar 

  132. Castagner B, Seeberger PH (2007) Top Curr Chem 278:289

    CAS  Google Scholar 

  133. Seeberger PH (2001) Solid support oligosaccharide synthesis and combinatorial carbohydrate libraries, Wiley Interscience, New York, p 308

    Google Scholar 

  134. Ratner DM, Swanson ER, Seeberger PH (2003) Org Lett 5:4717

    CAS  Google Scholar 

  135. Bousquet E, Khitri M, Lay L, Nicotra F, Panza L, Russo G (1998) Carbohydr Res 311:171

    CAS  Google Scholar 

  136. Sinnott ML (2007) Carbohydrate chemistry and biochemistry. RSC Publishing, Cambridge

    Google Scholar 

  137. Green LG, Ley SV (2000) In: Ernst B, Hart GW, Sinaÿ P (eds) Carbohydrates in chemistry and biology, vol 1. Wiley-VCH, Weinheim, p 427

    Google Scholar 

  138. Namchuk MN, McCarter JD, Becalski A, Andrews T, Withers SG (2000) J Am Chem Soc 122:1270

    CAS  Google Scholar 

  139. Dean KES, Kirby AJ, Komarov IV (2002) J Chem Soc Perkin Trans 2:337

    Google Scholar 

  140. Ford GP, Raghuveer KS (1988) Tetrahedron 44:7489

    CAS  Google Scholar 

  141. Olah GA, Prakash GKS, Krishnamurthy VV (1983) J Org Chem 48:5116

    CAS  Google Scholar 

  142. Wallace JE, Schroeder LR (1976) J Chem Soc Perkin Trans 2:1632

    Google Scholar 

  143. Horeau A, Kagan H-B, Vigneron JP (1968) Bull Soc Chim Fr 3795

    Google Scholar 

  144. Masamune S, Choy W, Peterson JS, Sita LR (1985) Angew Chem Int Ed 24:1

    Google Scholar 

  145. Spijker NM, van Boeckel CAA (1991) Angew Chem Int Ed 30:180

    Google Scholar 

  146. Bohé L, Crich D (2010) Trends Glycosci Glycotech 22:1

    Google Scholar 

  147. Crich D, Li H (2000) J Org Chem 56:801

    Google Scholar 

  148. McGarvey GJ, LeClair CA, Schmidtmann BA (2008) Org Lett 10:4727

    CAS  Google Scholar 

  149. Crich D, Sharma I (2008) Org Lett 10:4731

    CAS  Google Scholar 

  150. Ducros VM-A, Zechel DL, Murshudov GN, Gilbert HJ, Szabo L, Stoll D, Withers SG, Davies GJ (2002) Angew Chem Int Ed 41:2824

    CAS  Google Scholar 

  151. Zhu Y, Suits MDL, Thompson AJ, Chavan S, Dinev Z, Dumon C, Smith N, Moremen KW, Xiang Y, Siriwardena A, Williams SJ, Gilbert HJ, Davies GJ (2010) Nature Chem Biol 6:125

    CAS  Google Scholar 

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Acknowledgments

D.C. is especially grateful to the many co-workers, graduate students, and postdoctoral fellows, past and present, who have contributed significantly to the mannose project. He is equally grateful to the many colleagues, most notably Michael L. Sinnott, for their insightful comments and encouragement over the years.

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Authors and Affiliations

  1. Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 avenue de la Terrasse, 91198, Gif-sur-Yvette, France

    Sylvain Aubry, Kaname Sasaki & David Crich

  2. Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI, 48202, USA

    Indrajeet Sharma & David Crich

Authors
  1. Sylvain Aubry
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  2. Kaname Sasaki
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  3. Indrajeet Sharma
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  4. David Crich
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Correspondence to David Crich .

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Editors and Affiliations

  1. Natural Products and Glycotechnology Res, Swarthmore Road 4118, Durham, 27706, North Carolina, USA

    Bert Fraser-Reid

  2. Instituto de Quimica Orgánica General (C, Juan de la Cierva 3, Madrid, 28006, Spain

    J. Cristóbal López

Appendix

Appendix

figure ai
$$ \frac{\text{d}}{{{\text{d}}t}}[{\text{GT}}] = - {k_1}[{\text{GT}}] + {k_{ - 1}}[{\text{CIP}}] $$
$$ \frac{\text{d}}{{{\text{d}}t}}[{\text{CIP}}] = {k_1}[{\text{GT}}] - ({k_{ - 1}} + {k_2} + {k_\beta }[{\text{ROH}}])[{\text{CIP}}] + {k_{ - 2}}[{\text{SSIP}}]{[^{-} }{\text{OT}}f] $$
$$ \frac{\text{d}}{{{\text{d}}t}}[{\text{SSIP}}] = {k_2}[{\text{CIP}}] - ({k_{ - 2}}{[^{-} }{\text{OT}}f] + {k_\alpha }[{\text{ROH}}])[{\text{SSIP}}] $$

By the steady state approximation,

$$ \frac{\text{d}}{{{\text{d}}t}}[{P_\beta }] = \frac{{{k_\beta }{k_1}({k_\alpha }[{\text{ROH}}] + {k_{ - 2}}{[^{-} }{\text{OT}}\rm f])[{\text{GT}}]}}{{{k_\alpha }{k_\beta }{{[{\text{ROH}}]}^2} + ({k_\alpha }{k_{ - 1}} + {k_\alpha }{k_2} + {k_\beta }{k_{ - 2}}{[^{-} }{\text{OT}}\rm f])[{\text{ROH}}] + {k_{ - 1}}{k_{ - 2}}{[^{-} }{\text{OT}}\rm f]}} $$
$$ \frac{\text{d}}{{{\text{d}}t}}[{P_\alpha }] = \frac{{{k_\alpha }{k_1}{k_2}[{\text{GT}}]}}{{{k_\alpha }{k_\beta }{{[{\text{ROH}}]}^2} + ({k_\alpha }{k_{ - 1}} + {k_\alpha }{k_2} + {k_\beta }{k_{ - 2}}{[^{-} }{\text{OT}}\rm f])[{\text{ROH}}] + {k_{ - 1}}{k_{ - 2}}{[^{-} }{\text{OT}}\rm f]}} $$
$$ \frac{{{\text{(d}}[{P_\beta }])/{\text{d}}t}}{{({\text{d}}[{P_\alpha }])/{\text{d}}t}} = \frac{{{k_\alpha }}}{{{k_2}}}[{\text{ROH}}] + \frac{{{k_\beta }{k_{ - 2}}}}{{{k_\alpha }{k_2}}}{[^{-} }{\text{OT}}f] $$
$$ \frac{{{\text{(d}}[{P_\beta }])/{\text{d}}t}}{{({\text{d}}[{P_\alpha }])/{\text{d}}t}} = \frac{{{k_\alpha }}}{{{k_2}}}[{\text{ROH}}] + \frac{{{k_\beta }}}{{{k_\alpha }{k_2}}}{[^{-} }{\text{OT}}f] $$

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Aubry, S., Sasaki, K., Sharma, I., Crich, D. (2010). Influence of Protecting Groups on the Reactivity and Selectivity of Glycosylation: Chemistry of the 4,6-O-Benzylidene Protected Mannopyranosyl Donors and Related Species. In: Fraser-Reid, B., Cristóbal López, J. (eds) Reactivity Tuning in Oligosaccharide Assembly. Topics in Current Chemistry, vol 301. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2010_102

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