Synthesis of dl-erythro and threo-sphingosine-4,5-3H
β Scribed by Andrew E. Gal
- Publisher
- John Wiley and Sons
- Year
- 1967
- Tongue
- French
- Weight
- 420 KB
- Volume
- 3
- Category
- Article
- ISSN
- 0022-2135
No coin nor oath required. For personal study only.
β¦ Synopsis
DL-erythro-sphingosine and DL-threo-sphingosine specifically labelled with 3H in positions 4 and 5 were prepared. The synthesis of these compounds was based on a modification of a procedure published by Grob and Gadient. Quantitative separation of the sphingosines from acetylenic impurities was accomplished, and the physical constants of pure DL-erythro and threo sphingosines were determined. D-erythro sphingosine was prepared by resolving the DL racemate and it was found identical to the naturally occurring product.
π SIMILAR VOLUMES
## Isolated vield. \*) The free amine bases 1 4 are prone to air-oxidation and are difficult to handle.
D-erythro-sphingosine and D-esythro-sphinganine can be produced in protected form from serine by a synthetic approach in which the normal biological intermediate 3-ketosphinganine in protectyed form, is a key synthetic intermediate. The sequence is short and convergent, proceeds in good overall yiel
The chiral diazaborolidine 1 has been applied to the enantioselective syntheses of chloramphenicol ( 2) and (D)-threo-N-acetylsphingosine (3), a synthetic precursor of the diastereomeric (D)-sphingosines.