Di-tert-butylsilylene (DTBS) group-directed α-selective galactosylation unaffected by C-2 participating functionalities

被引:171
作者
Imamura, A
Ando, H
Korogi, S
Tanabe, G
Muraoka, O
Ishida, H
Kiso, M
机构
[1] Gifu Univ, Dept Appl Bioorgan Chem, Gifu 5011193, Japan
[2] Kinki Univ, Sch Pharmaceut Sci, Higashiosaka, Osaka 5778502, Japan
[3] JST, CREST, Gifu 5011193, Japan
基金
日本学术振兴会; 日本科学技术振兴机构;
关键词
alpha-galactosylation; neighboring participation; di-tert-butylsilylene group;
D O I
10.1016/S0040-4039(03)01647-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have discovered an unusual alpha-galactosylation using phenylthioglycoside of 4,6-O-di-tert-butylsilylene (DTBS)-protected galactose derivatives as a glycosyl donor, which was not hampered by the neighboring participation of C-2 acyl functionality such as NTroc and OBz. The power of the DTBS effect has been exemplified by the coupling reaction with various glycosyl acceptors. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6725 / 6728
页数:4
相关论文
共 32 条
[1]  
Aloui M, 2002, CHEM-EUR J, V8, P2608, DOI 10.1002/1521-3765(20020603)8:11<2608::AID-CHEM2608>3.0.CO
[2]  
2-4
[3]  
Baeschlin DK, 2000, CHEM-EUR J, V6, P172, DOI 10.1002/(SICI)1521-3765(20000103)6:1<172::AID-CHEM172>3.3.CO
[4]  
2-X
[5]  
Burkhart F, 2001, ANGEW CHEM INT EDIT, V40, P1274, DOI 10.1002/1521-3773(20010401)40:7<1274::AID-ANIE1274>3.0.CO
[6]  
2-W
[7]   Unusual α-glycosylation with galactosyl donors with a C2 ester capable of neighboring group participation [J].
Chen, LQ ;
Kong, FZ .
TETRAHEDRON LETTERS, 2003, 44 (18) :3691-3695
[8]   A convenient and highly stereoselective approach for α-galactosylation performed by galactopyranosyl dibenzyl phosphite with remote participating groups [J].
Cheng, YP ;
Chen, HT ;
Lin, CC .
TETRAHEDRON LETTERS, 2002, 43 (43) :7721-7723
[9]  
Dohi H, 2001, SYNLETT, P1446
[10]   GLYCOSYLATION USING GLUCOPYRANOSYL FLUORIDES AND SILICON-BASED CATALYSTS - SOLVENT DEPENDENCY OF THE STEREOSELECTION [J].
HASHIMOTO, S ;
HAYASHI, M ;
NOYORI, R .
TETRAHEDRON LETTERS, 1984, 25 (13) :1379-1382