Highly stereoselective 1,4-conjugate addition of organocopper reagents to methyl α-D-glucopyranoside derivatives tethering an unsaturated ester moiety at C-4 or C-6

Kiichiro Totani, Takayuki Nagatsuka, Kenichi Takao, Shigeru Ohba, Kin Ichi Tadano

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

(formula presented) The 1,4-conjugate additions of a variety of organocopper reagents to some 4-O-crotonyl derivatives of methyl α-D-glucopyranoside proceeded with a high level of diastereochemical induction to provide the adducts carrying a β-substituted butanoic ester at C-4. The 1,4-conjugate addition to a 6-O-crotonyl derivative afforded the adduct with reverse configuration at the β-carbon' to that obtained from the 4-O-crotonyl derivatives.

Original languageEnglish
Pages (from-to)1447-1450
Number of pages4
JournalOrganic Letters
Volume1
Issue number9
Publication statusPublished - 1999 Nov 4

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tethering
adducts
reagents
esters
Esters
Carbon
Derivatives
induction
carbon
configurations
methylglucoside
calcium ascorbate

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Highly stereoselective 1,4-conjugate addition of organocopper reagents to methyl α-D-glucopyranoside derivatives tethering an unsaturated ester moiety at C-4 or C-6. / Totani, Kiichiro; Nagatsuka, Takayuki; Takao, Kenichi; Ohba, Shigeru; Tadano, Kin Ichi.

In: Organic Letters, Vol. 1, No. 9, 04.11.1999, p. 1447-1450.

Research output: Contribution to journalArticle

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