A concise synthesis of C-glycosyl phosphate and phosphonate analogues of N-acetyl-α-D-glucosamine 1-phosphate

被引:12
作者
Gaurat, O
Xie, J
Valéry, JM
机构
[1] Univ Paris 06, Lab Chim Glucides, F-75005 Paris, France
[2] CNRS, F-75005 Paris, France
关键词
glycosyl phosphates; C-glycosyl phosphate; C-glycosyl phosphonate; amino C-glycosides;
D O I
10.1016/S0040-4039(99)02277-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An easy preparation of the C-glycosyl phosphate and phosphonate analogues of N-acetyl-alpha-D-glucosamine 1-phosphate is described. The readily available 3-(2' -acetamido-3',4',6' -tri-O-acetyl-2'-deoxy-alpha-D-glucopyranosyl)-1-propene 3 has been used as a common intermediate. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1187 / 1189
页数:3
相关论文
共 6 条
[1]   Stereoselective synthesis of the isosteric phosphono analogues of N-acetyl-alpha-D-glucosamine 1-phosphate and N-acetyl-alpha-D-mannosamine 1-phosphate [J].
Casero, F ;
Cipolla, L ;
Lay, L ;
Nicotra, F ;
Panza, L ;
Russo, G .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3428-3432
[2]   Stereocontrolled allylation of 2-amino-2-deoxy sugar derivatives by a free-radical procedure [J].
Cui, JR ;
Horton, D .
CARBOHYDRATE RESEARCH, 1998, 309 (04) :319-330
[3]   Diastereoselective synthesis of C-glycosylphosphonates via free-radical glycosylation [J].
Junker, HD ;
Fessner, WD .
TETRAHEDRON LETTERS, 1998, 39 (3-4) :269-272
[4]  
Nicotra F, 1998, CARBOHYDRATE MIMICS, P67
[5]   Synthesis of beta-C-glycosides of N-acetylglucosamine via Keck allylation directed by neighboring phthalimide groups [J].
Roe, BA ;
Boojamra, CG ;
Griggs, JL ;
Bertozzi, CR .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6442-6445