Selective synthesis of cerebrosides: (2S, 3R, 4E)-1-O-β-d-galactopyranosyl-N-(2′R and 2′S)-2′-hydroxytetracosanoyl-sphingenine View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1985-06

AUTHORS

Katsuya Koike, Mamoru Sugimoto, Yoshiaki Nakahara, Tomoya Ogawa

ABSTRACT

The cerebrosides were first isolated by Thudicum in 1874 and the structures were established by Carteret al. in 1950 (for review, see [2]). In 1961 Shapiro and Flowers [3] reported the first total synthesis of a cerebroside1 (Fig. 1) which was identified with the natural sample, only through comparison of their i.r. data. In order to confirm the absolute configuration at C-2′ of natural cerebroside1, we describe here an unambiguous synthesis of two stereoisomeric cerebrosides1 and2, and found that the1H-NMR spectra of the synthetic1 (Fig. 2) was completely identical with that of the natural cerebroside reported recently by Dabrowskiet al. [4]. In planning the synthetic route, the target structures1 and2 were disconnected at the dotted lines to give three key synthetic intermediates3, 4 and5 or6 (Fig. 1). More... »

PAGES

105-108

Journal

TITLE

Glycoconjugate Journal

ISSUE

2

VOLUME

2

Author Affiliations

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/bf01050467

DOI

http://dx.doi.org/10.1007/bf01050467

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1004639257


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