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

Kenichi Takao, Hiroshi Saegusa, Kin Ichi Tadano

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)57-69
Number of pages13
JournalJournal of Carbohydrate Chemistry
Volume20
Issue number1
DOIs
Publication statusPublished - 2001

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Spiro Compounds
Glucose
Substrates
1,2-5,6-di-O-isopropylidene-D-glucofuranose

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Organic Chemistry

Cite this

Orthoester Claisen rearrangement of a D-glucose-derived spirocyclic substrate. / Takao, Kenichi; Saegusa, Hiroshi; Tadano, Kin Ichi.

In: Journal of Carbohydrate Chemistry, Vol. 20, No. 1, 2001, p. 57-69.

Research output: Contribution to journalArticle

Takao, Kenichi ; Saegusa, Hiroshi ; Tadano, Kin Ichi. / Orthoester Claisen rearrangement of a D-glucose-derived spirocyclic substrate. In: Journal of Carbohydrate Chemistry. 2001 ; Vol. 20, No. 1. pp. 57-69.
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