Facile Cu(OTf)2-catalyzed preparation of per-O-acetylated hexopyranoses with stoichiometric acetic anhydride and sequential one-pot anomeric substitution to thioglycosides under solvent-free conditions

被引：123
作者：
Tai, CA
Kulkarni, SS
Hung, SC [1 ]
机构：
[1] Acad Sinica, Inst Chem, Taipei 115, Taiwan
[2] Natl Chung Cheng Univ, Dept Chem, Chiayi 621, Taiwan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 22期
关键词：
D O I：
10.1021/jo030073b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Solvent-free per-O-acetylation of hexoses with a stoichiometric amount of acetic anhydride employing 0.03 mol % Cu(OTf)(2) proceeded in high yields (90-99%) at room temperature to give exclusively pyranosyl products as an anomeric mixture, the alpha/beta ratio of which was dependent on the temperature and amount of catalyst used. Sequential anomeric substitution with p-thiocresol in the presence of BF3.etherate gave the thioglycosides, isolated exclusively or predominantly as one anomer in 66-75% yields.
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收藏
页码：8719 / 8722
页数：4
相关论文
共 47 条
[1]  
*ALDR CHEM CO, 1993, ALDR LIB H NMR C NMR, V1, P1056
[2]  
Bhaskar PM, 1999, SYNLETT, P129
[3]   Per-O-acetylation of sugars catalysed by montmorillonite K-10 [J].
Bhaskar, PM ;
Loganathan, D .
TETRAHEDRON LETTERS, 1998, 39 (15) :2215-2218
[4]   Chemical synthesis of GDP-L-galactose and analogues [J].
Binch, H ;
Stangier, K ;
Thiem, J .
CARBOHYDRATE RESEARCH, 1998, 306 (03) :409-419
[5]   Acylation of alcohols with acetic anhydride catalyzed by TaCl5:: Some implications in kinetic resolution [J].
Chandrasekhar, S ;
Ramachander, T ;
Takhi, M .
TETRAHEDRON LETTERS, 1998, 39 (20) :3263-3266
[6]  
Chauhan KK, 1999, SYNLETT, P1743
[7]   Catalytic nucleophilic acyl substitution of anhydrides by amphoteric vanadyl triflate [J].
Chen, CT ;
Kuo, JH ;
Li, CH ;
Barhate, NB ;
Hon, SW ;
Li, TW ;
Chao, SD ;
Liu, CC ;
Li, YC ;
Chang, IH ;
Lin, JS ;
Liu, CJ ;
Chou, YC .
ORGANIC LETTERS, 2001, 3 (23) :3729-3732
[8]   Heterogeneous catalysis in acetylation of alcohols and phenols promoted by zirconium sulfophenyl phosphonate [J].
Curini, M ;
Epifano, F ;
Marcotullio, MC ;
Rosati, O ;
Rossi, M .
SYNTHETIC COMMUNICATIONS, 2000, 30 (07) :1319-1329
[9]   USE OF FERRIC-CHLORIDE IN CARBOHYDRATE REACTIONS .2. ACETYLATION OF CARBOHYDRATES USING FERRIC-CHLORIDE IN ACETIC-ANHYDRIDE [J].
DASGUPTA, F ;
SINGH, PP ;
SRIVASTAVA, HC .
CARBOHYDRATE RESEARCH, 1980, 80 (02) :346-349
[10]   An efficient route to per-O-acetylated hexofuranoses [J].
Ferrières, V ;
Gelin, M ;
Boulch, R ;
Toupet, L ;
Plusquellec, D .
CARBOHYDRATE RESEARCH, 1998, 314 (1-2) :79-83
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