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
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
[11]   Oxidation of 1,2-dihydroquinolines under mild and heterogeneous conditions [J].
Damavandi, JA ;
Zolfigol, MA ;
Karami, B .
SYNTHETIC COMMUNICATIONS, 2001, 31 (20) :3183-3187
[12]   Studies on novel synthetic methodologies, part 59.: A simple and efficient method for α-bromination of carbonyl compounds using N-bromosuccinimide in the presence of silica-supported sodium hydrogen sulfate as a heterogeneous catalyst [J].
Das, B ;
Venkateswarlu, K ;
Mahender, G ;
Mahender, L .
TETRAHEDRON LETTERS, 2005, 46 (17) :3041-3044
[13]   A simple and facile stereoselective synthesis of (Z)- and (E)-allyl halides catalyzed by silica supported sodium hydrogen sulfate:: factors influencing the yields and stereochemistry of allyl halides [J].
Das, B ;
Banerjee, J ;
Ravindranath, N .
TETRAHEDRON, 2004, 60 (38) :8357-8361
[14]   Chemoselective deprotection of trityl ethers using silica-supported sodium hydrogen sulfate [J].
Das, B ;
Mahender, G ;
Kumar, VS ;
Chowdhury, N .
TETRAHEDRON LETTERS, 2004, 45 (36) :6709-6711
[15]   Silica-supported sodium hydrogen sulfate and Amberlyst-15:: Two efficient heterogeneous catalysts for single-step synthesis of 4(3H)-quinazolinones from anthranilic acid, ortho esters, and amines under solvent free conditions [J].
Das, B ;
Banerjee, J .
CHEMISTRY LETTERS, 2004, 33 (08) :960-961
[16]   A simple, efficient and highly selective deprotection of t-butyldimethylsilyl (TBDMS) ethers using silica supported sodium hydrogen sulfate as a heterogeneous catalyst [J].
Das, Biswanath ;
Reddy, K. Ravinder ;
Thirupathi, P. .
TETRAHEDRON LETTERS, 2006, 47 (33) :5855-5857
[17]   A METHOD FOR THE SELECTIVE REDUCTION OF CARBOHYDRATE 4,6-O-BENZYLIDENE ACETALS [J].
DENINNO, MP ;
ETIENNE, JB ;
DUPLANTIER, KC .
TETRAHEDRON LETTERS, 1995, 36 (05) :669-672
[18]   New one-carbon degradative transformation of β-alkyl-β-azido alcohols [J].
Fan, QH ;
Ni, NT ;
Li, Q ;
Zhang, LH ;
Ye, XS .
ORGANIC LETTERS, 2006, 8 (05) :1007-1009
[19]  
Fletcher H G., 1963, METHODS CARBOHYDR CH, V2, P307
[20]   SOME ASPECTS OF REGIOSELECTIVE, STEREOSELECTIVE, AND CHEMOSELECTIVE REACTIONS IN CARBOHYDRATE-CHEMISTRY [J].
GAREGG, PJ .
PURE AND APPLIED CHEMISTRY, 1984, 56 (07) :845-858