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Enantioselective synthesis of D-erythro-sphingosine

✍ Scribed by Bruno Bernet; Andrea Vasella


Book ID
108382361
Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
244 KB
Volume
24
Category
Article
ISSN
0040-4039

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πŸ“œ SIMILAR VOLUMES


Enantioselective Synthesis of D-erythro-
✍ Radomir Julina; Thomas Herzig; Bruno Bernet; Andrea Vasella πŸ“‚ Article πŸ“… 1986 πŸ› John Wiley and Sons 🌐 German βš– 398 KB

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

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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.

Asymmetric synthesis of D-erythro-sphing
✍ Ulrich Groth; Ulrich SchΓΆllkopf; Thomas Tiller πŸ“‚ Article πŸ“… 1991 πŸ› Elsevier Science 🌐 French βš– 511 KB

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.