Summary.
A route is investigated for the synthesis of 3-O-allyl-1,4-anhydro-5-O-tert-butyldiphenylsilyl-2-deoxy-D-erythro-pent-1-enitol. The highest overall yield was obtained when 5′-O-(tert-butyldiphenylsilyl)thymidine was converted to the corresponding furanoid glycal and subsequently 3-O-allylated.
Similar content being viewed by others
References
RE Ireland S Thaisrivongs N Varier CS Wilcox (1980) J Org Chem 45 48 Occurrence Handle10.1021/jo01289a012
EJ Corey G Goto (1980) Tetrahedron Lett 21 3463 Occurrence Handle10.1016/S0040-4039(00)78715-6
Daves GD Jr (1992) Carbohydrates, Synthetic Methods and Applications in Medicinal Chemistry. VCH, New York, pp 49–65
K Chow S Danishefsky (1990) J Org Chem 55 4211 Occurrence Handle10.1021/jo00300a049
CU Kim PF Misco (1992) Tetrahedron Lett 33 5733 Occurrence Handle10.1016/0040-4039(92)89018-8
A El-Laghdach Y Diás S Castillon (1993) Tetrahedron Lett 34 2821 Occurrence Handle10.1016/S0040-4039(00)73571-4
U Hacksell GD Daves (1985) Prog Med Chem 22 1 Occurrence Handle3915364
CU Kim PF Misco (1992) Tetrahedron Lett 33 5733 Occurrence Handle10.1016/0040-4039(92)89018-8
GD Daves SuffixJr CC Cheng (1976) Prog Med Chem 13 303 Occurrence Handle801779
S Moran RXF Ren S Rumney ET Kool (1997) J Am Chem Soc 119 2056 Occurrence Handle10.1021/ja963718g
RK Ness HG Fletcher (1963) J Org Chem 28 435
K Bischofberger RH Hall (1976) Carbohydr Res 52 223 Occurrence Handle10.1016/S0008-6215(00)85964-9
JC Cheng U Hacksell GD Daves SuffixJr (1985) J Org Chem 50 2778 Occurrence Handle10.1021/jo00215a036
W Abramski MJ Chmielewski (1994) Carbohydr Chem 13 125
M Kassou S Castillón (1994) Tetrahedron Lett 35 5513 Occurrence Handle10.1016/S0040-4039(00)73538-6
JA Walker JJ Chen DS Wise LB Townsed (1996) J Org Chem 61 2219 Occurrence Handle10.1021/jo951376b
Larsen E, Jørgensen PT, Sofan MA, Pedersen EB (1994) Synthesis 1037
AM Cameron SB Cush RP Hammer (1997) J Org Chem 62 9065 Occurrence Handle10.1021/jo970947s
S Marcotte B Gerard X Pannecoucke C Feasson J-C Quirion (2001) Synthesis 6 929 Occurrence Handle10.1055/s-2001-13419
V Serebryany A Karpeisky J Matulic-Adamic L Beigelman (2002) Synthesis 12 1652
RS Coleman ML Madaras (1998) J Org Chem 63 5700 Occurrence Handle10.1021/jo980478+
M Tingoli B Panunzi F Santacroce (1999) Tetrahedron Lett 40 9329 Occurrence Handle10.1016/S0040-4039(99)01975-9
T Lan LW McLaughlin (2001) Bioorg Chem 29 198 Occurrence Handle10.1006/bioo.2001.1209
P Raboisson A Baurand J-P Cazenave C Gachet D Schultz B Spiess J-J Bourguignon (2002) J Org Chem 67 8063 Occurrence Handle10.1021/jo026268l Occurrence Handle12423133
D Hutter SA Benner (2003) J Org Chem 68 9839 Occurrence Handle10.1021/jo034900k Occurrence Handle14656120
A Mayer CJ Leumann (2003) Nucleosides, Nucleotides & Nucleic Acids 22 1919
RS Coleman MA Mortensen (2003) Tetrahedron Lett 44 1215 Occurrence Handle10.1016/S0040-4039(02)02791-0
J-S Han TL Lowary (2003) J Org Chem 68 4116 Occurrence Handle12737605
P Bisseret J-G Boiteau J Eustache (2003) Tetrahedron Lett 44 2351 Occurrence Handle10.1016/S0040-4039(03)00241-7
V Fehring MY Chan IA O’Neil R Cosstick (2000) J Chem Soc Perkin Trans 1 19 3185 Occurrence Handle10.1039/b007099h
Author information
Authors and Affiliations
Corresponding author
Additional information
On leave from Chemistry Department, Faculty of Education Kafr El-Sheikh branch Tanta University, Kafr El-Sheikh, Egypt
Rights and permissions
About this article
Cite this article
Aly, Y., Pedersen, E. Synthesis of a New Furanoid Glycal Auxiliary. Monatsh. Chem. 136, 1641–1644 (2005). https://doi.org/10.1007/s00706-005-0342-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-005-0342-7