Synthesis of (+)-galactostatin and (+)-1-deoxygalactostatin utilizing L-quebrachitol as a chiral building block

Noritaka Chida, Tetsuya Tanikawa, Takahiko Tobe, Seiichiro Ogawa

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

The stereoselective conversion of the naturally occurring optically active cyclitol, L-quebrachitol 1, into galactosidase inhibitors, (+)-galactostatin 2 and (+)-1-deoxygalactostatin 3 is described; the key steps in this synthesis are (i) stereoselective introduction of an azido function and (ii) regioselective ring cleavage of the cyclohexane ring of 1 by way of the Baeyer-Villiger reaction.

Original languageEnglish
Pages (from-to)1247-1248
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number10
DOIs
Publication statusPublished - 1994

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Cyclitols
Galactosidases
Cyclohexane
quebrachitol
5-amino-5-deoxygalactopyranose

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Synthesis of (+)-galactostatin and (+)-1-deoxygalactostatin utilizing L-quebrachitol as a chiral building block. / Chida, Noritaka; Tanikawa, Tetsuya; Tobe, Takahiko; Ogawa, Seiichiro.

In: Journal of the Chemical Society, Chemical Communications, No. 10, 1994, p. 1247-1248.

Research output: Contribution to journalArticle

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