A practical synthesis of β-D-mannopyranosides

被引:44
作者
Fürstner, A [1 ]
Konetzki, I [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
carbohydrates; glycosidation; trichloroacetimidates; triflates; sonochemistry;
D O I
10.1016/S0040-4039(98)01163-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An indirect yet highly efficient protocol for the P-D-mannosylation of sterically hindered alcohols is reported. Trichloroacetimidate 5 is used a key building block which is converted into the desired mannosides 9 via triflates 8 by an ultrasound promoted beta-D-gluco --> beta-D-manno inversion process. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5721 / 5724
页数:4
相关论文
共 42 条
[1]   SYNTHESIS OF BETA-MANNOPYRANOSIDES BY INTRAMOLECULAR AGLYCON DELIVERY [J].
BARRESI, F ;
HINDSGAUL, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9376-9377
[2]  
BARRESI F, 1992, SYNLETT, P759
[3]   SYNTHESIS OF 4-O-BETA-D-MANNOPYRANOSYL-L-RHAMNOPYRANOSE [J].
BEBAULT, GM ;
DUTTON, GGS .
CARBOHYDRATE RESEARCH, 1974, 37 (02) :309-319
[4]   SYNTHESIS AND REACTIONS OF CARBOHYDRATE TRIFLUOROMETHANESULFONATES (CARBOHYDRATE TRIFLATES) [J].
BINKLEY, RW ;
AMBROSE, MG .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1984, 3 (01) :1-49
[5]   STUDY OF C-13H COUPLING-CONSTANTS IN HEXOPYRANOSES [J].
BOCK, K ;
PEDERSEN, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (03) :293-299
[6]   Formation of beta-mannopyranosides of primary alcohols using the sulfoxide method [J].
Crich, D ;
Sun, SX .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4506-4507
[7]   Direct synthesis of beta-mannopyranosides by the sulfoxide method [J].
Crich, D ;
Sun, SX .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1198-1199
[8]   Direct formation of β-mannopyranosides and other hindered glycosides from thioglycosides [J].
Crich, D ;
Sun, SX .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :435-436
[9]  
CRICH D, 1994, J ORG CHEM, V59, P6728
[10]   STEREOCONTROLLED SYNTHESIS OF THE PENTASACCHARIDE CORE STRUCTURE OF ASPARAGINE-LINKED GLYCOPROTEIN OLIGOSACCHARIDE BASED ON A HIGHLY CONVERGENT STRATEGY [J].
DAN, A ;
ITO, Y ;
OGAWA, T .
TETRAHEDRON LETTERS, 1995, 36 (41) :7487-7490