Studies on the synthesis of apoptolidin A. 2. Synthesis of the disaccharide unit

被引:18
作者
Handa, Masaki [1 ]
Smith, William J., III [2 ]
Roush, William R. [1 ]
机构
[1] Scripps Florida, Dept Chem, Jupiter, FL 33458 USA
[2] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
关键词
D O I
10.1021/jo7022526
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Disaccharide 3 correspoinding to the disaccharide unit of apoptolidin A. has been synthesized via the regio- and stereoselective TBS-OTf-promoted beta-glycosidation reaction of 2,6-dideoxy-2-iodo-beta-glucopyranosyl acetate (5) and p-methoxybenzyl 2,6-dideoxy-2-iodo-3-C-methyl-alpha-mannopyranoside (11).
引用
收藏
页码:1036 / 1039
页数:4
相关论文
共 45 条
[21]  
Nicolaou KC, 2001, ANGEW CHEM INT EDIT, V40, P3849, DOI 10.1002/1521-3773(20011015)40:20<3849::AID-ANIE3849>3.0.CO
[22]  
2-M
[23]  
Nicolaou KC, 2001, ANGEW CHEM INT EDIT, V40, P3854, DOI 10.1002/1521-3773(20011015)40:20<3854::AID-ANIE3854>3.0.CO
[24]  
2-D
[25]   Enantioselective preparation of the C1-C11 fragment of apoptolidin [J].
Paquette, WD ;
Taylor, RE .
ORGANIC LETTERS, 2004, 6 (01) :103-106
[26]   SHORT STEREOSELECTIVE SYNTHESIS OF L-NOGALOSE [J].
PARKER, KA ;
MESCHWITZ, SM .
CARBOHYDRATE RESEARCH, 1988, 172 (02) :319-326
[27]  
ROUSH WR, 1993, SYNLETT, P264
[28]   2-deoxy-2-iodo-α-mannopyranosyl and -talopyranosyl acetates:: Highly stereoselective glycosyl donors for the synthesis of 2-deoxy-α-glycosides [J].
Roush, WR ;
Narayan, S .
ORGANIC LETTERS, 1999, 1 (06) :899-902
[29]   A highly stereoselective synthesis of 2-deoxy-β-glycosides using 2-deoxy-2-iodo-glucopyranosyl acetate donors [J].
Roush, WR ;
Bennett, CE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (14) :3541-3542
[30]   2-Deoxy-2-iodo- and 2-deoxy-2-bromo-α-glucopyranosyl trichloroacetimidates:: Highly reactive and stereoselective donors for the synthesis of 2-deoxy-β-glycosides [J].
Roush, WR ;
Gung, BW ;
Bennett, CE .
ORGANIC LETTERS, 1999, 1 (06) :891-893