Synthesis of C-aryl and C-alkyl glycosides using glycosyl phosphates

被引:65
作者
Palmacci, ER [1 ]
Seeberger, PH [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ol0158462
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Mannosyl and glucosyl phosphate donors were successfully used in constructing C-aryl linkages common to many natural products via a Lewis acid induced Fries like rearrangement, The rearrangement was stereo and regiospecific, yielding only one C-glycoside product. C-Alkyl glycoside carbohydrate mimetics were generated by using silicon derived C-nucleophiles and glycosyl phosphates.
引用
收藏
页码:1547 / 1550
页数:4
相关论文
共 16 条
[1]   Solid-phase oligosaccharide synthesis: Preparation of complex structures using a novel linker and different glycosylating agents [J].
Andrade, RB ;
Plante, OJ ;
Melean, LG ;
Seeberger, PH .
ORGANIC LETTERS, 1999, 1 (11) :1811-1814
[2]   THE SYNTHESIS OF HETEROBIFUNCTIONAL LINKERS FOR THE CONJUGATION OF LIGANDS TO MOLECULAR PROBES [J].
BERTOZZI, CR ;
BEDNARSKI, MD .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4326-4329
[3]   A RAPID AND EFFICIENT SYNTHESIS OF 1,2-TRANS-BETA-LINKED GLYCOSIDES VIA BENZYL-PROTECTED OR BENZOYL-PROTECTED GLYCOPYRANOSYL PHOSPHATES [J].
HASHIMOTO, S ;
HONDA, T ;
IKEGAMI, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (11) :685-687
[4]   BERGENIN, A C-GLYCOPYRANOSYL DERIVATIVE OF 4-0-METHYLGALLIC ACID [J].
HAY, JE ;
HAYNES, LJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1958, (JUN) :2231-2238
[5]  
HOFFMANN MG, 1985, LIEBIGS ANN CHEM, P2403
[6]   STEREOSELECTIVE SYNTHESIS OF 3-(D-GLYCOPYRANOSYL)PROPENES BY USE OF ALLYLSILANES [J].
HOSOMI, A ;
SAKATA, Y ;
SAKURAI, H .
CARBOHYDRATE RESEARCH, 1987, 171 :223-232
[7]   Samarium diiodide mediated coupling of glycosyl phosphates with carbon radical or anion acceptors - Synthesis of C-glycosides [J].
Hung, SC ;
Wong, CH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (22) :2671-2674
[8]  
Levy D.D.E., 1995, CHEM C GLYCOSIDES, V13
[9]   Synthesis of sialyl Lewis X mimetics and related structures using the glycosyl phosphite methodology and evaluation of E-selectin inhibition [J].
Lin, CC ;
Shimazaki, M ;
Heck, MP ;
Aoki, S ;
Wang, R ;
Kimura, T ;
Ritzen, H ;
Takayama, S ;
Wu, SH ;
WeitzSchmidt, G ;
Wong, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (29) :6826-6840
[10]  
MAHLING JA, 1993, SYNTHESIS-STUTTGART, P325