Short syntheses of D-deoxymannojirimycin and D-mannonolactam from L-gulonolactone and of L-deoxymannojirimycin and L-mannonolactam from D-gulonolactone
โ Scribed by George W.J. Fleet; Nigel G. Ramsden; David R. Witty
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 223 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
๐ SIMILAR VOLUMES
The (R R)-6-alkoxy-2-triphenylphosphoniomethyl-dihydropyran iodide 2 and the --di-acetonide of 6-deoxy-aldehydo-L-glucose 3 are elaborated from (R,R)-tartrate and D-gulonolactone, resp., and subsequently joined to yield (+)-anamarine (l), identical with the Hyptis-derived product.
Interconversion of the ends of D-ribese 2 afforded in 6 steps and 45% overall yield L-ribose 1, from which 2-deoxy L-ribose 12 was easily prepared. In addition, the inexpensive L-arabinose 13 was also converted into 2-deoxy L-ribose 12 via a reductive radical rearrangement of the arabinopyranosyl br