The synthesis of 7-carbonyl homologues of 1-deoxynojirimycin
β Scribed by Amuri Kilonda; Frans Compernolle; Suzanne Toppet; Georges J. Hoornaert
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 311 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
π SIMILAR VOLUMES
An asymmetric synthesis of (+)-l-deoxynojirimycin (1) in 14 steps starting from diene ( 5) is described. The key transformations in the sequence are a Sharpless dihydroxylation and epoxidation followed by a regio-and stereoselective aminolysis of vinyl epoxide 11 to give piperidine 12.
The synthesis of 2-acetamido-1 ,Zdideoxynojirimycin (Zacetamido-1,2,5-trideoxy-1,5-imino-D-glucitol) by a double inversion procedure starting from l-deoxynojirimycin is reported. The key intermediates were the selectively protected N-benzyl-l,5-dideoxy-l,5-imino-4,6-0-isopropylidene-~-mannitol, the