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StereoselectiveO-glycosylation oftrans-4-hydroxy-l-proline derivatives promoted by silver zeolite

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Abstract

Trans-4-hydroxy-l-proline has been converted to four imino- and carboxyl-blocked derivatives which are suitable for the synthesis of 4-O-glycosyl conjugates. Reaction of these derivatives with 2,3,5-tri-O-benzyl-α-l-arabinofuranosyl chloride in the presence of a silver zeolite promoter yielded the blocked β-furanosyl amino-acid conjugates. Deprotection gavetrans-4-(β-l-arabinofuranosyloxy)-l-proline which was characterised as its crystalline isopropyl ester.13C-NMR Data are presented for the compounds described.

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Authors and Affiliations

  1. Bourne Laboratory, Royal Holloway and Bedford New College, TW20 0EX, Egham, Surrey, England

    Paul Finch & Aloysius H Siriwardena

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  1. Paul Finch
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  2. Aloysius H Siriwardena
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Finch, P., Siriwardena, A.H. StereoselectiveO-glycosylation oftrans-4-hydroxy-l-proline derivatives promoted by silver zeolite. Glycoconjugate J 6, 477–487 (1989). https://doi.org/10.1007/BF01053771

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  • DOI: https://doi.org/10.1007/BF01053771

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