title: Total Synthesis of Marine Glycosphingolipid Vesparioside B.
abstract: The first total synthesis of a major component of marine glycolipid vesparioside B ( Scheme 1 , 1, R1 = n-C22H45, R2 = n-C14H29) has been accomplished through a convergent [4 + 3] coupling strategy. Key steps included stereoselective installment of a set of challenging 1,2-cis-glycoside bonds. A 2-quinolinecarbonyl-assisted α-galactosylation and a novel β-arabinosylation were developed, respectively, to synthesize the α-galactofuranosidic and the β-arabinopyranosidic linkages. Furthermore, a 4,6-O-benzylidene-controlled α-galactopyranosylation reaction allowed the efficient connection of the left tetrasaccharide donor 2 with the right disaccharide lipid acceptor 3, hence leading to the total synthesis of 1.
authors.affiliation: Department of Chemistry of Medicinal Natural Products, and Key Laboratory of Drug Targeting, Ministry of Education, West China School of Pharmacy, Sichuan University , Chengdu 610041, China.
authors.forename: Peng-Cheng
authors.initials: PC
authors.lastname: Gao
authors.affiliation: Department of Chemistry of Medicinal Natural Products, and Key Laboratory of Drug Targeting, Ministry of Education, West China School of Pharmacy, Sichuan University , Chengdu 610041, China.
authors.forename: San-Yong
authors.initials: SY
authors.lastname: Zhu
authors.affiliation: Department of Chemistry of Medicinal Natural Products, and Key Laboratory of Drug Targeting, Ministry of Education, West China School of Pharmacy, Sichuan University , Chengdu 610041, China.
authors.forename: Hui
authors.initials: H
authors.lastname: Cao
authors.affiliation: Department of Chemistry of Medicinal Natural Products, and Key Laboratory of Drug Targeting, Ministry of Education, West China School of Pharmacy, Sichuan University , Chengdu 610041, China.|State Key Laboratory of Biotherapy, West China Hospital, Sichuan University , Chengdu 610041, China.
authors.forename: Jin-Song
authors.initials: JS
authors.lastname: Yang
mesh_terms: D000818:Animals; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006860:Hydrogen Bonding; D011161:Porifera / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy
chemical_list: D006028:Glycosphingolipids