๐”– Bobbio Scriptorium
โœฆ   LIBER   โœฆ

ChemInform Abstract: Synthesis of 1,6-Dideoxynojirimycin, 1,6-Dideoxy-D-allo-nojirimycin, and 1,6-Dideoxy-D-gulo-nojirimycin via Asymmetric Hetero-Diels-Alder Reactions.

โœ Scribed by A. DEFOIN; H. SARAZIN; J. STREITH

Book ID
112033777
Publisher
John Wiley and Sons
Year
2010
Weight
33 KB
Volume
27
Category
Article
ISSN
0931-7597

No coin nor oath required. For personal study only.

๐Ÿ“œ SIMILAR VOLUMES

Synthesis of 1,6-Dideoxynojirimycin, 1,6
Synthesis of 1,6-Dideoxynojirimycin, 1,6-Dideoxy-D-allo-nojirimycin, and 1,6-Dideoxy-D-gulo-nojirimycin via Asymmetric Hetero-Diels-Alder Reactions
โœ Albert Defoin; Hervรฉ Sarazin; Jacques Streith ๐Ÿ“‚ Article ๐Ÿ“… 1996 ๐Ÿ› John Wiley and Sons ๐ŸŒ German โš– 503 KB

## Abstract Asymmetric __Dielsโ€Alder__ reaction of sorbaldehyde __O__โ€methyloxime 1d with chiral chloronitroso derivative 2 of Dโ€mannose, followed by osmylation of the primary cycloadduct, led to diol 6a with excellent enantioselectivity (ee > 99%; __Scheme 1__). Catalytic hydrogenolysis of 6a gave

6-Deoxy-nojirimycin and 6-deoxy-gulo-noj
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
โœ Albert Defoin; Hervรฉ Sarazin; Jacques Streith ๐Ÿ“‚ Article ๐Ÿ“… 1997 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 871 KB

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 aAhwt of h~ldicnal dime~ylac~tai to aehiral or enantiometieally pure nitroso-derivatives) led to ~xynojirimycin and 6-deoxy-gu/o..