H2SO4-SiO2: Highly Efficient and Reusable Catalyst for per-O-Acetylation of Carbohydrates Under Solvent-Free Conditions

被引：22

作者：

Zhang, Jianbo ^{[1
]}

Zhang, Bo ^{[1
]}

Zhou, Jiafen ^{[1
]}

Li, Juan ^{[1
]}

Shi, Chunjuan ^{[1
]}

Huang, Ting ^{[1
]}

Wang, Zhongfu ^{[2
]}

Tang, Jie ^{[1
]}

机构：

[1] E China Normal Univ, Dept Chem, Shanghai 200062, Peoples R China

[2] Northwestern Univ, Sch Life Sci, Xian 710069, Peoples R China

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2011年 / 30卷 / 03期

基金：

上海市自然科学基金;

关键词：

Sulfuric acid on silica gel (H2SO4-SiO2); Per-O-acetylation; Carbohydrate; Acetic anhydride; SULFURIC-ACID; SUGARS; MONOSACCHARIDES; THIOGLYCOSIDES; SILICA; DERIVATIVES; ACETOLYSIS; CHEMISTRY; ALCOHOLS; ACETATE;

D O I：

10.1080/07328303.2011.621042

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Sulfuric acid immobilized on silica gel (H2SO4-SiO2) was used as an efficient promoter for per-O-acetylation of carbohydrates with acetic anhydride under solvent-free conditions. The substrates include not only monosaccharides and disaccharides, but also glycosides. The catalyst is recyclable and stable at room temperature, and the reaction protocol is simple, is cost-effective, and gives good isolated yield with high purity. The large-scale reactions also proceeded conveniently and in high yields.

引用

页码：165 / 177

页数：13

共 35 条

[1] THE REDUCTION OF SUGARS WITH SODIUM BOROHYDRIDE [J].

ABDELAKHER, M ;

HAMILTON, JK ;

SMITH, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (10) :4691-4692

[2] Per-O-acetylation of sugars catalyzed by Ce(OTf)3 [J].

Bartoli, G ;

Dalpozzo, R ;

De Nino, A ;

Maiuolo, L ;

Nardi, M ;

Procopio, A ;

Tagarelli, A .

GREEN CHEMISTRY, 2004, 6 (04) :191-192

[3] A Versatile Synthesis of 5′-Functionalized Nucleosides Through Regioselective Enzymatic Hydrolysis of Their Peracetylated Precursors [J].

Bavaro, Teodora ;

Rocchietti, Silvia ;

Ubiali, Daniela ;

Filice, Marco ;

Terreni, Marco ;

Pregnolato, Massimo .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (12) :1967-1975

[4] A challenge for green chemistry: designing molecules that readily dissolve in carbon dioxide [J].

Beckman, EJ .

CHEMICAL COMMUNICATIONS, 2004, (17) :1885-1888

[5] Per-O-acetylation of sugars catalysed by montmorillonite K-10 [J].

Bhaskar, PM ;

Loganathan, D .

TETRAHEDRON LETTERS, 1998, 39 (15) :2215-2218

[6] A straightforward α-selective aromatic glycosylation and its application for stereospecific synthesis of 4-methylumbelliferyl α-T-antigen [J].

Chang, Shih-Sheng ;

Lin, Chun-Cheng ;

Li, Yaw-Kuen ;

Mong, Kwok-Kong Tony .

CARBOHYDRATE RESEARCH, 2009, 344 (04) :432-438

[7] Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides [J].

Chao, Chin-Sheng ;

Chen, Min-Chun ;

Lin, Shih-Che ;

Mong, Kwok-Kong T. .

CARBOHYDRATE RESEARCH, 2008, 343 (05) :957-964

[8] Vinyl acetate and sodium carbonate as a fast and efficient catalyst for per-O-acetylation of monosaccharides [J].

Chen, Li ;

Zhang, Jianbo ;

Shi, Chunjuan ;

Wang, Xiaohu ;

Zhang, Bo ;

Tang, Jie .

JOURNAL OF CHEMICAL RESEARCH, 2008, (07) :380-382

[9]

COHEN RB, 1952, J BIOL CHEM, V195, P239

[10] Syntheses of 1-thio-D-xylose and D-ribose esters of diorganoarsinous acids and their anticancer activity [J].

Gao, Mingzhang ;

Chen, Yiwen ;

Tan, Songde ;

Reibenspies, Joseph H. ;

Zingaro, Ralph A. .

HETEROATOM CHEMISTRY, 2008, 19 (02) :199-206

← 1 2 3 4 →