Efficient formation and cleavage of benzylidene acetals by sodium hydrogen sulfate supported on silica gel

被引：33
作者：
Niu, Youhong
Wang, Ning
Cao, Xiaoping
Ye, Xin-Shan
机构：
[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[3] Lanzhou Univ, Dept Chem, Lanzhou 730000, Peoples R China
来源：
SYNLETT | 2007年 / 13期
关键词：
sodium hydrogen sulfate supported on silica gel; protection; deprotection; benzylidene acetals; carbohydrate;
D O I：
10.1055/s-2007-984903
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
NaHSO4 center dot SiO2 was used as an efficient heterogeneous catalyst for both the formation and the cleavage of benzylidene acetals. This catalyst is compatible with many functional or protective groups. Under different solvent systems, either the formation or the cleavage of benzylidene acetals was carried out smoothly in excellent yields and with good chemoselectivity.
引用
收藏
页码：2116 / 2120
页数：5
相关论文
共 58 条
[21]   INVESTIGATIONS OF THE FORMATION OF CYCLIC ACETAL AND KETAL DERIVATIVES OF D-RIBONO-1,4-LACTONE AND 2-DEOXY-D-RIBONO-1,4-LACTONE [J].
HAN, SY ;
JOULLIE, MM ;
PETASIS, NA ;
BIGORRA, J ;
CORBERA, J ;
FONT, J ;
ORTUNO, RM .
TETRAHEDRON, 1993, 49 (02) :349-362
[22]   REACTION OF O-BENZYLIDENE SUGARS WITH N-BROMOSUCCINIMIDE .2. SCOPE AND SYNTHETIC UTILITY IN METHYL 4,6-O-BENZYLIDENEHEXOPYRANOSIDE SERIES [J].
HANESSIAN, S ;
PLESSAS, NR .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (04) :1035-+
[23]  
HANESSIAN S, 1968, ADV CHEM SER, P159
[24]   1,3-ANHYDRO-2,4-METHYLENE-D,L-XYLITOL AND RELATED COMPOUNDS [J].
HANN, RM ;
RICHTMYER, NK ;
DIEHL, HW ;
HUDSON, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (01) :561-566
[25]  
HARTUNG WH, 1953, ORG REACTIONS, V7, P263
[26]  
KENNE L, 1980, METHODS CARBOHYDR CH, V8, P317
[27]  
Larock R. C., 1999, COMPREHENSIVE ORGANI, P1019
[28]   CHEMOSELECTIVE STEREOSELECTIVE AND REGIOSELECTIVE HYDROGENOLYSIS OF CARBOHYDRATE BENZYLIDENE ACETALS - SYNTHESIS OF BENZYL ETHERS OF BENZYL ALPHA-D-MANNOPYRANOSIDES METHYL BETA-D-MANNOPYRANOSIDES AND BENZYL ALPHA-D-RHAMNOPYRANOSIDE BY RING CLEAVAGE OF BENZYLIDENE DERIVATIVES WITH THE LIALH4-ALCL3 REAGENTEN [J].
LIPTAK, A ;
IMRE, J ;
HARANGI, J ;
NANASI, P ;
NESZMELYI, A .
TETRAHEDRON, 1982, 38 (24) :3721-3727
[29]   A simple and facile chemo- and regioselective deprotection of acetonides using silica supported sodium hydrogen sulfate as a heterogeneous catalyst [J].
Mahender, G ;
Ramu, R ;
Ramesh, C ;
Das, B .
CHEMISTRY LETTERS, 2003, 32 (08) :734-735
[30]   ELECTRO-DEPROTECTION - ELECTROCHEMICAL REMOVAL OF PROTECTING GROUPS [J].
MAIRANOVSKY, VG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (05) :281-292
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