Stereoselective mannich-like reactions of ester enolates generated on sugar templates: A novel access to a key intermediate for 1β-methylcarbapenem synthesis

Daisuke Sasaki, Daisuke Sawamoto, Kenichi Takao, Kin ichi Tadano, Masayuki Okue, Keiichi Ajito

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The Mannich-like reactions of the enolates generated from 2,3-di-O-protected 6-deoxy-4-O-propionyl-α-D-glucopyranosides with (3R,4R)-4-acetoxy-3-((R)-1-(t-butyldimethylsilyloxy)ethyl ]azetidin-2-one were investigated. The corresponding 2,3-di-O-methyl derivative provided the Mannich adduct in good to excellent stereoselectivity. From the major adduct, the azetidin-2-one incorporating an α-methyl acetic acid side chain at the C-4 position with ß-configuration was obtained by alkaline hydrolysis. This product, (3S,4S)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl 1-4-1(R)-1-carboxyethylJazetidin-2-one, is a useful intermediate for the 1 ß-methylcarbapenem synthesis.

Original languageEnglish
Pages (from-to)103-110
Number of pages8
JournalHeterocycles
Volume72
Publication statusPublished - 2007 Apr 13

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Stereoselectivity
Sugars
Acetic Acid
Hydrolysis
Esters
Derivatives
1 beta-methylcarbapenem

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stereoselective mannich-like reactions of ester enolates generated on sugar templates : A novel access to a key intermediate for 1β-methylcarbapenem synthesis. / Sasaki, Daisuke; Sawamoto, Daisuke; Takao, Kenichi; Tadano, Kin ichi; Okue, Masayuki; Ajito, Keiichi.

In: Heterocycles, Vol. 72, 13.04.2007, p. 103-110.

Research output: Contribution to journalArticle

Sasaki, Daisuke ; Sawamoto, Daisuke ; Takao, Kenichi ; Tadano, Kin ichi ; Okue, Masayuki ; Ajito, Keiichi. / Stereoselective mannich-like reactions of ester enolates generated on sugar templates : A novel access to a key intermediate for 1β-methylcarbapenem synthesis. In: Heterocycles. 2007 ; Vol. 72. pp. 103-110.
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