6-Deoxy- allo-nojirimycin in the racemic and d-series, 6-deoxy- d,l- talo-nojirimycin, their 1-deoxyderivatives and 6-deoxy-2- d,l-allosamine via hetero- Diels-Alder cycloadditions

Diels-Alder cycloaddition of hexadienal dimethylacetal 3 to achiral acylnitroso-dienophile 5a gave the racemic cycloadducts 7a-c and, to chiral chloronitroso-dienophile 6, enantiomerically pure D-10a as sole adduct. Simple chemical transformations led to 6-deoxy-2- d,l-allosamine 15b, to 6-deoxy- d,...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 53; no. 40; pp. 13769 - 13782
Main Authors Defoin, Albert, Sarazin, Hervé, Streith, Jacques
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.10.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
(+)-GALACTOSTATIN
(+)-NOJIRIMYCIN
ACYLNITROSO DIENOPHILES
ENZYMES
CARBOHYDRATE-RECOGNITION
1-DEOXY DERIVATIVES
NOJIRIMYCIN
(+)-1-DEOXYGALACTOSTATIN
SUGARS
Online AccessGet full text

Cover

More Information
Summary:Diels-Alder cycloaddition of hexadienal dimethylacetal 3 to achiral acylnitroso-dienophile 5a gave the racemic cycloadducts 7a-c and, to chiral chloronitroso-dienophile 6, enantiomerically pure D-10a as sole adduct. Simple chemical transformations led to 6-deoxy-2- d,l-allosamine 15b, to 6-deoxy- d,l and d- allo-nojirimycin 15a, D-15a, to 6-deoxy- d,l- talo-nojirimycin 15c as well as to their 1-deoxy-derivatives 16a, D-16a, 16c via their crystalline 1-deoxy-1-sulfonic acid derivatives (sulfite adducts). Amino-sugars 16a,c are mixtures of α- and β-anomers and of the corresponding imines. Achiral and asymmetric Diels-Alder reactions from hexa-2,4-dienal with nitroso dienophiles led after simple chemical transformations to the title compounds
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00897-1