A convenient synthesis of disaccharides containing furanoside units

被引：49

作者：

Velty, R ^{[1
]}

Benvegnu, T ^{[1
]}

Gelin, M ^{[1
]}

Privat, E ^{[1
]}

Plusquellec, D ^{[1
]}

机构：

[1] ECOLE NATL SUPER CHIM RENNES,CNRS,LAB CHIM ORGAN & SUBST NAT,F-35700 RENNES,FRANCE

来源：

CARBOHYDRATE RESEARCH | 1997年 / 299卷 / 1-2期

关键词：

n-pentenyl furanosides; glycosidation; glycosyl donors; disaccharides; furanoside units;

D O I：

10.1016/S0008-6215(96)00268-6

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：

Pent-4-enyl 2,3,5,6-tetra-O-acetyl-D-glycofuranosides were synthesized in a one-pot reaction by a ferric chloride-promoted glycosylation of 4-penten-1-ol with D-glucose, D-mannose, and D-galactose, respectively, in heterogeneous media, followed by in situ acetylation. These n-pentenyl glycosides are efficient glycofuranosyl donors and have therefore been used for the subsequent synthesis of various furanosyl-pyranoside type or furanosyl-furanoside type disaccharides related to archaebacterial glycolipids and protozoa glycoconjugates. (C) 1997 Elsevier Science Ltd.

引用

页码：7 / 14

页数：8

共 26 条

[1] HAWORTH MEMORIAL LECTURE - SUGAR-CATION COMPLEXES - STRUCTURE AND APPLICATIONS
ANGYAL, SJ
[J]. CHEMICAL SOCIETY REVIEWS, 1980, 9 (04) : 415 - 428
[2] N-PENTENYL FURANOSIDES - SYNTHESIS AND GLYCOSIDATION REACTIONS OF SOME GALACTO DERIVATIVES
ARASAPPAN, A
FRASERREID, B
[J]. TETRAHEDRON LETTERS, 1995, 36 (44) : 7967 - 7970
[3] LECYTHOPHORIN, A POTENT INHIBITOR OF BLUE-STAIN FUNGI, FROM THE HYPHOMYCETOUS FUNGUS LECYTHOPHORA-HOFFMANNII
AYER, WA
KAWAHARA, N
[J]. TETRAHEDRON LETTERS, 1995, 36 (44) : 7953 - 7956
[4] A NEW SYNTHESIS OF D-GLYCOSIDURONATES FROM UNPROTECTED D-URONIC ACIDS
BERTHO, JN
FERRIERES, V
PLUSQUELLEC, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (13) : 1391 - 1393
[5] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF MONOSACCHARIDES
BOCK, K
PEDERSEN, C
[J]. ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1983, 41 : 27 - 66
[6] PROTON AND C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA OF SOME BENZOYLATED ALDOHEXOSES
DACCORSO, NB
THIEL, IME
SCHULLER, M
[J]. CARBOHYDRATE RESEARCH, 1983, 124 (02) : 177 - 184
[7] DEARRUDA MV, 1989, EUR J BIOCHEM, V182, P413, DOI 10.1111/j.1432-1033.1989.tb14847.x
[8] SYNTHESIS OF ALPHA-D-GALACTOFURANOSYL PHOSPHATE
DELEDERKREMER, RM
NAHMAD, VB
VARELA, O
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) : 690 - 692
[9] GALACTOFURANOSE-CONTAINING GLYCOCONJUGATES IN TRYPANOSOMATIDS
DELEDERKREMER, RM
COLLI, W
[J]. GLYCOBIOLOGY, 1995, 5 (06) : 547 - 552
[10] A NEW SYNTHESIS OF O-GLYCOSIDES FROM TOTALLY O-UNPROTECTED GLYCOSYL DONORS
FERRIERES, V
BERTHO, JN
PLUSQUELLEC, D
[J]. TETRAHEDRON LETTERS, 1995, 36 (16) : 2749 - 2752

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