Stereoselective α-alkylation of methyl 6-deoxy-3,4-di-O-(tert-butyldimethylsilyl)-2-O-(2-methyl-3-oxobutanoyl)-α-d-glucopyranoside

Yoko Akashi, Ken ichi Takao, Kin ichi Tadano

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Allylation and benzylation at the α-carbon of α-methylated acetoacetyl (2-methyl-3-oxobutanoyl) group incorporated into the 2-OH of methyl 6-deoxy-3,4-O-(tert-butyldimethylsilyl)-α-d-glucopyranoside provided the respective α,α-differentially alkylated acetoacetyl derivatives, both with high diastereoselectivity. Thus-obtained doubly alkylated products possess an all-carbon quaternary stereogenic center with an absolute stereochemistry opposite to that introduced by using the 4-O-acetoacetyl regioisomer as the alkylation substrate.

Original languageEnglish
Pages (from-to)1139-1142
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number10
DOIs
Publication statusPublished - 2009 Mar 11

Keywords

  • Asymmetric synthesis
  • Carbohydrates
  • Chiral auxiliary
  • Stereoselective synthesis
  • α-Alkylation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Stereoselective α-alkylation of methyl 6-deoxy-3,4-di-O-(tert-butyldimethylsilyl)-2-O-(2-methyl-3-oxobutanoyl)-α-d-glucopyranoside'. Together they form a unique fingerprint.

Cite this