Synthesis of 1,5-dideoxy-1,5-imino- d-galactitol from l-sorbose

A facile new synthesis of 1-deoxygalactonojirimycin ( 1) [1,5-dideoxy-1,5-imino- d-galactitol] is described. The l-sorbose derivative ( 15) is epimerised at C-3 and converted, via the l-tagatofuranose ( 18) into the deoxyazide ( 20). Reduction of azide ( 20) and deprotection affords 1-deoxygalactono...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 34; no. 22; pp. 3609 - 3612
Main Authors Furneaux, Richard H, Tyler, Peter C, Whitehouse, Lynley A
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.05.1993
Elsevier
Subjects
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
INHIBITION
1-DEOXYNOJIRIMYCIN
CASTANOSPERMINE
ALKALOIDS
Chemical reduction
Sodium Azides
Epimerization
Nitrogen heterocycle
Aminoglycoside
Six membered ring
Ketose
Online AccessGet full text

Cover

More Information
Summary:A facile new synthesis of 1-deoxygalactonojirimycin ( 1) [1,5-dideoxy-1,5-imino- d-galactitol] is described. The l-sorbose derivative ( 15) is epimerised at C-3 and converted, via the l-tagatofuranose ( 18) into the deoxyazide ( 20). Reduction of azide ( 20) and deprotection affords 1-deoxygalactonojirimycin ( 1). The L-sorbose derivative (15) is epimerised at C-3 and converted, via the L-tagatofuranose (18), into the deoxyazide (20). Reduction of (20) and deprotection affords 1-deoxygalactonojirimycin (1).
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)73649-5