Unusual sugars of the GPL-type antigen of Mycobacterium avium serovar 19. Stereoselective synthesis of methyl 6-deoxy-3-C-methyl-2,4-di-O-methyl-α-L-mannopyranoside and its C-4 epimer

K. Gyergyói, A. Tóth, I. Bajza, A. Lipták

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Completely reversed stereoselectivity of reduction of methyl 6-deoxy-2,3-O-isopropylidene-3-C-methyl-α-L-mannopyranoside (2) and its deisopropylidenated derivative (7) was observed. Compound 2 gave exclusively the L-talo-isomer (3) with NaBH4 in MeOH, but the reduction of 7 with NaBH4 in acetic acid resulted in the L-manno-derivative 8. It is assumed that in the first case the stereoselectivity is determined by the steric accessibility of the carbonyl group, while in the second case free OH-groups direct the selectivity of the reduction by complexation or ligand exchange.

Original languageEnglish
Pages (from-to)127-128
Number of pages2
JournalSynlett
Issue number2
DOIs
Publication statusPublished - Feb 1998

ASJC Scopus subject areas

  • Organic Chemistry

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