DABCO: an efficient promoter for the acetylation of carbohydrates and other substances under solvent-free conditions

被引：15

作者：

Ch, Ratnasekhar ^{[1
]}

Tyagi, Mohit ^{[1
]}

Patil, Premanand Ramrao ^{[1
]}

Kartha, K. P. Ravindranathan ^{[1
]}

机构：

[1] Natl Inst Pharmaceut Educ & Res, Dept Med Chem, Sas Nagar 160062, Punjab, India

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 44期

关键词：

DABCO; Acetylation; Carbohydrates; Alcohols; PER-O-ACETYLATION; PRIMARY HYDROXYL PROTECTION; CATALYZED ACETYLATION; SUGAR ACETATES; ALCOHOLS; ACYLATION; THIOGLYCOSIDES; POWERFUL; 4-DIALKYLAMINOPYRIDINES; PERACETYLATION;

D O I：

10.1016/j.tetlet.2011.08.141

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple, mild and efficient solvent-free method for the acetylation of carbohydrates, and their partially protected derivatives, as well as non-carbohydrate substances in excellent yields in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) is described with the advantage of tolerance to various functional groups, short reaction time and ease of product isolation. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：5841 / 5846

页数：6

共 52 条

[41] Sugar acetates as novel, renewable CO2-philes [J].

Raveendran, P ;

Wallen, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) :7274-7275

[42] 4-DIALKYLAMINOPYRIDINES - SUPER ACYLATION AND ALKYLATION CATALYSTS [J].

SCRIVEN, EFV .

CHEMICAL SOCIETY REVIEWS, 1983, 12 (02) :129-161

[43] Fe2(SO4)3•xH2O-catalyzed per-O-acetylation of sugars compatible with acid-labile protecting groups adopted in carbohydrate chemistry [J].

Shi, Lei ;

Zhang, Guisheng ;

Pan, Feng .

TETRAHEDRON, 2008, 64 (11) :2572-2575

[44] 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 [J].

Tai, CA ;

Kulkarni, SS ;

Hung, SC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (22) :8719-8722

[45] Acylation of carbohydrates over Al2O3:: preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides [J].

Tiwari, P ;

Misra, AK .

CARBOHYDRATE RESEARCH, 2006, 341 (03) :339-350

[46] Efficient acetylation of carbohydrates promoted by imidazole [J].

Tiwari, P ;

Kumar, R ;

Maulik, PR ;

Misra, AK .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (20) :4265-4270

[47] Reversible charge-accelerated oxy-cope rearrangements [J].

Tsui, HC ;

Paquette, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9968-9977

[48]

Wolfrom M.L., 1963, METHODS CARBOHYDR CH, V2, P211

[49] Reactions on a solid surface.: A simple, economical, and efficient acylation of alcohols and Amines over Al2O3 [J].

Yadav, VK ;

Babu, KG .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (02) :577-580

[50] Anomeric reactivity-based one-pot oligosaccharide synthesis: A rapid route to oligosaccharide libraries [J].

Ye, XS ;

Wong, CH .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) :2410-2431

← 1 2 3 4 5 6 →