Concise synthesis of clarhamnoside, a novel glycosphingolipid isolated from the marine sponge Agela clathrodes.
The first total synthesis of a novel alpha-galactoglycosphingolipid clarhamnoside has been achieved through a straightforward strategy. A thiogalactosyl donor with a benzylidene group at C-4 and C-6 and nonparticipating p-methoxybenzyl group at C-2 was successfully employed in the stereocontrolled syntheses of alpha-GalGSLs. The N-Phth-protected trifluoroacetimidate donor for terminal disaccharide was successfully applied in constructing the [GalNAc beta-(1-->6)-Gal] glycosidic linkage.
Ding
Ning
N
Key Laboratory of Marine Drugs, The Ministration of Education of China, School of Pharmacy, Ocean University of China, Qingdao 266003, China.
Li
Chunxia
C
Liu
Yunpeng
Y
Zhang
Zaihong
Z
Li
Yingxia
Y
D047230:Agelas / Q000737:chemistry*; D000818:Animals; D001597:Benzylidene Compounds / Q000737:chemistry; D038983:Galactolipids / Q000737:chemistry; D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000302:isolation & purification; D006028:Glycosphingolipids / Q000138:chemical synthesis
D001597:Benzylidene Compounds; D038983:Galactolipids; D005699:Galactosylceramides; D006028:Glycosphingolipids; C483920:clarhamnoside