Synthesis and reduction of carbohydrate benzylidene hemithioacetal diastereomers with LiAlH4-AlCl3

Peter Fugedi, A. Lipták

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Reduction of methyl 2-O-benzyl-endo- (11) and -exo-3-O-4-S-benzylidene-4,6- dideoxy-4-thio-α-D-galactopyranoside (12) gives the same S-benzyl derivative (6), but with very different reaction rates, indicating that the configuration of the acetal carbon considerably influences the reactivity of the acetal oxygen atoms.

Original languageEnglish
Pages (from-to)1234-1235
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number24
Publication statusPublished - 1980

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Acetals
Carbohydrates
Reaction rates
Derivatives
Atoms
Carbon
Oxygen
Galactose
aluminum chloride
lithium aluminum hydride

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

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title = "Synthesis and reduction of carbohydrate benzylidene hemithioacetal diastereomers with LiAlH4-AlCl3",
abstract = "Reduction of methyl 2-O-benzyl-endo- (11) and -exo-3-O-4-S-benzylidene-4,6- dideoxy-4-thio-α-D-galactopyranoside (12) gives the same S-benzyl derivative (6), but with very different reaction rates, indicating that the configuration of the acetal carbon considerably influences the reactivity of the acetal oxygen atoms.",
author = "Peter Fugedi and A. Lipt{\'a}k",
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language = "English",
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journal = "Chemical Communications",
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publisher = "Royal Society of Chemistry",
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AU - Lipták, A.

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N2 - Reduction of methyl 2-O-benzyl-endo- (11) and -exo-3-O-4-S-benzylidene-4,6- dideoxy-4-thio-α-D-galactopyranoside (12) gives the same S-benzyl derivative (6), but with very different reaction rates, indicating that the configuration of the acetal carbon considerably influences the reactivity of the acetal oxygen atoms.

AB - Reduction of methyl 2-O-benzyl-endo- (11) and -exo-3-O-4-S-benzylidene-4,6- dideoxy-4-thio-α-D-galactopyranoside (12) gives the same S-benzyl derivative (6), but with very different reaction rates, indicating that the configuration of the acetal carbon considerably influences the reactivity of the acetal oxygen atoms.

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