Efficient syntheses of a series of glycosphingolipids with 1,2-trans-glycosidic linkages

被引：15

作者：

Liu, Yunpeng ^{[1
]}

Ding, Ning ^{[1
]}

Xiao, Hualing ^{[1
]}

Li, Yingxia ^{[1
]}

机构：

[1] Ocean Univ China, Sch Pharm, Minist Educ China, Key Lab Marine Drugs, Qingdao 266003, Peoples R China

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2006年 / 25卷 / 06期

关键词：

glycosphingolipid with 1,2-trans-glycosidic linkage; Schmidt's; glycosyl trichloroacetimidate; Azido-sphingosine; glycosylation; conformation;

D O I：

10.1080/07328300600859825

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of glycosphingolipids with 1,2-trans-glycosidic linkages were synthesized in the presence of neighboring group participation using trichloroacetimidates as glycosyl donors and an azido-sphingosine as the glycosyl acceptor. During the preparation of the target compounds, it was found that the alpha-L-arabinopyranosyl unit in target 7e and intermediates 7b - 7d existed in the C-1(4) conformation and that the b-L-fucopyranosyl unit in 10e adopted the C-4(1) conformation.

引用

页码：471 / 489

页数：19

共 50 条

[31] SYNTHESES IN 4H-IMIDAZO(1,2-A)-1,4-BENZODIAZEPINE SERIES
MAFFRAND, JP
FERRAND, G
ELOY, F
TETRAHEDRON LETTERS, 1973, 14 (36) : 3449 - 3452
[32] Syntheses of 1,2-diamino and 1,2-aminoalcohol derivatives in the piperidine and pyrrolidine series as anti-amnesic agents
Zhao, S
Freeman, JP
Bacon, CL
Fox, GB
O'Driscoll, E
Foley, AG
Kelly, J
Farrell, U
Regan, C
Mizsak, SA
Szmuszkovicz, J
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (08) : 1647 - 1654
[33] Efficient syntheses of imidazolo[1,2-a]pyridines and -[2,1-a]isoquinolines
Katritzky, AR
Qiu, GF
Long, QH
He, HY
Steel, PJ
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26): : 9201 - 9205
[34] Convenient syntheses of 1,2-trans selenoglycosides using isoselenuronium salts as glycosylselenenyl transfer reagents
Kumar, Ambati Ashok
Illyes, Tuende Zita
Koever, Katalin E.
Szilagyi, Laszlo
CARBOHYDRATE RESEARCH, 2012, 360 : 8 - 18
[35] BACTERIAL CAROTENOIDS .48. TOTAL SYNTHESES OF CAROTENES OF 1,2-DIHYDRO SERIES
EIDEM, A
BUCHECKER, R
KJOSEN, H
LIAAENJENSEN, S
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, 29 (10): : 1015 - 1023
[36] SYNTHESIS OF POLYSACCHARIDES WITH 1,2-CIS-GLYCOSIDIC LINKAGES BY TRITYL-THIOCYANATE POLYCONDENSATION - STEREOREGULAR ALPHA-(1-6)-D-GLUCAN
KOCHETKOV, NK
MALYSHEVA, NN
KLIMOV, EM
DEMCHENKO, AV
TETRAHEDRON LETTERS, 1992, 33 (03) : 381 - 384
[37] Efficient synthesis of (ω-mercaptoalkyl 1,2-trans-glycosides from sugar peracetates
Murakami, Teiichi
Hirono, Reiko
Sato, Yukarl
Furusawa, Kiyotaka
CARBOHYDRATE RESEARCH, 2007, 342 (08) : 1009 - 1020
[38] SYNTHESES OF DISACCHARIDES WITH (1-]4)-BETA GLYCOSIDIC LINKAGES RELATED TO THE 4-SULFATES AND 6-SULFATES AND THE 4,6-DISULFATES OF CHONDROITIN
ZSISKA, M
MEYER, B
CARBOHYDRATE RESEARCH, 1991, 215 (02) : 261 - 277
[39] STEREOSELECTIVE SYNTHESES OF 1,2-TRANS-1-THIOGLYCOSES USING ALUMINUM-CHLORIDE - EVIDENCE FOR 1,2-CIS-1-CHLOROGLYCOPYRANOSYLPERACETATES AS THE ACTUAL REACTION INTERMEDIATES
RAJANIKANTH, B
SESHADRI, R
TETRAHEDRON LETTERS, 1987, 28 (20) : 2295 - 2296
[40] Two-dimensional relayed-rotating-frame overhauser spectroscopy 1H NMR experiments for the selective identification of 1,2-glycosidic linkages in polysaccharides
Cipollo, JF
Trimble, RB
Rance, M
Cavanagh, J
ANALYTICAL BIOCHEMISTRY, 2000, 278 (01) : 52 - 58

← 1 2 3 4 5 →