Synthesis and transformations of (1R,2R,3S,4R)-4-O-benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol: synthesis of (1S,2R,3S,4R)-4-amino-2,3-O-isopropylidene-1,2,3-cyclopentanetriol
✍ Scribed by José Marco-Contelles; Ma.Mercedes Rodríguez-Fernández
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- English
- Weight
- 533 KB
- Volume
- 8
- Category
- Article
- ISSN
- 0957-4166
No coin nor oath required. For personal study only.
✦ Synopsis
Synthesis and transformations of (1R,2R,3S,4R)-4-O-
benzylhydroxylamino-2,3-O-isopropylidene-1,2,3-cyclopentanetrioh synthesis of (1S,2R,3S,4R)-4-amino-2,3-O-isopropylidene-l,2,3cyclopentanetriol
📜 SIMILAR VOLUMES
The tide compounds were prepared from key intermediates readily obtained by the stereoselective Diels-Alder reaction of (Z)-2-pbenyl-4-[(S)-2,2-dimethyl-l,3dioxolan-4-ylmethylene]-5(4H)-oxazolone, a chiral az-lactone derived from (R)glyceraldehyde and cyclopentadiene.
Methoxycyclitol 4 was acetalized in a non-classical one-pot idene moiety was realised in two steps via the corresponding ethylidene acetals 8 and 9; the ethylidene function was procedure with chloral/dicyclohexylcarbodiimide forming the 4-epi derivative 6. The stepwise deprotection of removed with a