Synthesis of a New Cerebroside from a Chondropsis sp. Sponge

• Published in: Chemical & pharmaceutical bulletin Vol. 39; no. 6; pp. 1385 - 1391
• Main Authors: HONDA, Masanori, UEDA, Yoshitaka, SUGIYAMA, Shigeo, KOMORI, Tetsuya
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 1991; Pharmaceutical Soc Japan; Maruzen; Japan Science and Technology Agency
• Subjects: (R)-benzyl-2, 3-epoxypropyl ether; absolute stereochemistry; animal metabolism; asymmetric synthesis; biochemical analysis; biosynthesis; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Chondropsis; Chondropsis sp; Exact sciences and technology; galactosyl ceramide; glycosphingolipid; hypotensive activity; hystidine decarboxylase; Life Sciences & Biomedicine; Lipids; Marine; metabolites; Organic chemistry; Pharmacology & Pharmacy; Physical Sciences; phytosphingosine; Preparations and properties; Science & Technology; sponge; synthesis; STEREOISOMERS; CHONDROPSIS SP; HYPOTENSIVE ACTIVITY; ANTIULCEROGENIC ACTIVITY; STEREOCHEMISTRY; GLYCOSPHINGOLIPID; ABSOLUTE STEREOCHEMISTRY; GALACTOSYL CERAMIDE; DICYCLOHEXYLCARBODIIMIDE; ASYMMETRIC SYNTHESIS; SPONGE; ABSOLUTE-CONFIGURATION; ALLYLIC ALCOHOLS; BIOLOGICALLY-ACTIVE GLYCOSIDES; ASYMMETRIC EPOXIDATION; PHYTOSPHINGOSINE; (R)-BENZYL-2,3-EPOXYPROPYL ETHER; SPHINGOSINE RELATIVES; HYSTIDINE DECARBOXYLASE; Cerebroside; Marine environment; Hypotensive drug; Asymmetric synthesis; Absolute configuration; Ceramide; Sphingoglycolipid; Glycoside; Glycol
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.39.1385

A cerebroside, 1-O-(β-D-galactopyranosyloxy)-(2S, 3S, 4R, 6E)-2-[(R)-2-hydroxytetracosanoylamino]-17-methyl-6-octadecene-3, 4-diol (2), was asymmetrically synthesized from isobutyraldehyde. On the basis of a comparison of the physical data, the absolute structure of a new cerebroside 1b from a Chondropsis sp. sponge is thought to be the same at that of 2.