Orthoester Claisen rearrangement of a D-glucose-derived spirocyclic substrate

Ken Ichi Takao, Hiroshi Saegusa, Kin Ichi Tadano

研究成果: Article査読

4 被引用数 (Scopus)

抄録

The Claisen rearrangement of a spiro compound 1 derived from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, with triethyl orthopropionate afforded the rearrangement products 4, 5, and 6 as a 1:2.5:10 diastereomeric mixture. The reaction of 1 with trimethyl orthobutyrate provided a 1:3 mixture of 7 and 8. In both cases, the σ-bond formation proceeded predominantly from the β-side. This stereochemical outcome was opposite to that observed in the case of the rearrangement of 1 with triethyl orthoacetate.

本文言語English
ページ(範囲)57-69
ページ数13
ジャーナルJournal of Carbohydrate Chemistry
20
1
DOI
出版ステータスPublished - 2001

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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