Synthetic Studies on Sphingolipids. Part 5. Stereocontrolled Synthesis of Novel Phytosphingosine-Type Glucosaminocerebrosides. -Phytosphingosine (X) is prepared by an improved route involving regioselective O-methanesulfonation and diastereoselective Grignard addition as key steps. The novel glucos
Stereocontrolled synthesis of novel phytosphingosine-type glucosaminocerebrosides
โ Scribed by Teiichi Murakami; Kazuhiro Taguchi
- Book ID
- 104209040
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 1006 KB
- Volume
- 55
- Category
- Article
- ISSN
- 0040-4020
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โฆ Synopsis
D-r/bo-Phytosphingosine I was conveniently synthesized from N-benzoyl-D-gluco~mnine $ by an improved route in which regioselective O-methanesulfonation and dias~ereoselective Grignard addition are involved as key steps. Using a synthetic intermediate of 1, novel D-rJbo-pbytosphingosinetype glycolipids 2a and 2b, unnatural homologues of antifungal cerebrosides Halicylindrosides, were efficiently synthesized in a stereoeontrolled mannar.
๐ SIMILAR VOLUMES
AbstracL Deryrhro-Sphingosine (1) and phytosphingosine (2) have been efficiently synthesized from D-glucosamine by utilizing its whole carbon skeleton and functional groups. In this synthetic route, regioselective alkylation of the epoxy-tosylate 9 was achieved with a copper(I)-catalyzed Grignard re