Literature DB >> 18821764

Syntheses of alpha- and beta-C-glucopyranosyl serines from a common intermediate.

Ernest G Nolen1, Laurence A Donahue, Rebecca Greaves, Trevor A Daly, David R Calabrese.   

Abstract

A versatile synthesis leading to either C-linked alpha- or beta-glucopyranosyl serines is presented from a common, advanced synthetic intermediate. Cyclization of the penultimate carbinol onto the alkene and methanolysis of the lactone yields selectively the alpha-linkage. A transposition of these last steps leads to the beta-linked isomer selectively.

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Year:  2008        PMID: 18821764     DOI: 10.1021/ol802009v

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  1 in total

1.  Synthesis of β-C-GlcNAc Ser from β-C-Glc Ser.

Authors:  Ernest G Nolen; Leyan Li; Kristopher V Waynant
Journal:  J Org Chem       Date:  2013-06-17       Impact factor: 4.354

  1 in total

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