Asymmetric synthesis of D-erythro-sphingosine
✍ Scribed by Ulrich Groth; Ulrich Schöllkopf; Thomas Tiller
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 511 KB
- Volume
- 47
- Category
- Article
- ISSN
- 0040-4020
No coin nor oath required. For personal study only.
✦ Synopsis
D-erythro-Sphingosine 9 is a building block of cerebrosides and glycosphingolipids and was synthesized in 5 steps via an asymmetric aldol addition of the lithiated bislactim ether of cyclo-(L-Val-Gly) 4 to (2E)-hexadecenal(3) in an overall yield of 21 %. I.
📜 SIMILAR VOLUMES
2,4-Di-O-protected Pthreose, readily avaiZabZe from D-galactose, is a versatile intermediate for D-erythro-sphingosine syntheses via trans-selective Wittig reaction, azide introduction at the unprotected hydroxyZic group, and subsequent azide reduction.
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