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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

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✦ 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


Synthesis of d-erythro-sphingosines
✍ Richard R. Schmidt; Peter Zimmermann 📂 Article 📅 1986 🏛 Elsevier Science 🌐 French ⚖ 184 KB

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 D-erythro-sphingosine and D
✍ Robert V. Hoffman; Junhua Tao 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 212 KB

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