6-DEOXY-NOJIRIMYCIN AND 6-DEOXY-GULO-NOJIRIMYCIN IN THE RACEMIC AND D-SERIES, D-FUCO-NOJIRIMYCIN AND THEIR 1-DEOXYDERIVATIVES VIA HETERO-DIELS-ALDER CYCLOADDITIONS

Authors
DEFOIN A SARAZIN H STREITH J
Citation
A. Defoin et al., 6-DEOXY-NOJIRIMYCIN AND 6-DEOXY-GULO-NOJIRIMYCIN IN THE RACEMIC AND D-SERIES, D-FUCO-NOJIRIMYCIN AND THEIR 1-DEOXYDERIVATIVES VIA HETERO-DIELS-ALDER CYCLOADDITIONS, Tetrahedron, 53(40), 1997, pp. 13783-13796
Citations number
42
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
40
Year of publication
1997
Pages
13783 - 13796
Database
ISI
SICI code
0040-4020(1997)53:40<13783:6A6ITR>2.0.ZU;2-L
Abstract
Nucleophilic ring opening of the cyclic sulfates (+/-)-9c and D-9c and of the epoxide (+/-)-13, or double substitution of the bis-triflate D -10 (derived from the Diels-Alder adduct of hexadienal dimethylacetal to achiral or enantiomerically pure nitroso-derivatives) led to 6-deox y-nojirimycin and 6-deoxy-gulo-nojirimycin in the racemic and D-series , to D-fuco-nojirimycin and to their 1-deoxyderivatives via their crys talline 1-deoxy-1-sulfonic acid derivatives (sulfite adducts). 6-Deoxy -nojirimycin and its isomers are mixtures of alpha- and beta-anomers a nd of the corresponding imine. (C) 1997 Elsevier Science Ltd.