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.
Synthesis of an orthogonally protected d-(+)-erythro-sphingosine
β Scribed by Joseph M Gargano; Watson J Lees
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 64 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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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.
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
In their synthesis of dihydrosphingosine, Rozrsh and Adum [ 131 observed the formation of a I :1 mixture of two isomeric oxazolidinones resulting from an intramolecular transacylation: under our conditions, however, only 9 was obtained. We thank Prof. Dr. W . Roush for a preliminary communication of