Mild and efficient method for the cleavage of benzylidene acetals using HClO4-SiO2 and direct conversion of acetals to acetates

被引：67

作者：

Agnihotri, Geetanjali ^{[1
]}

Misra, Anup Kumar ^{[1
]}

机构：

[1] Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226001, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 22期

关键词：

carbohydrate; debenzylidenation; acetylation; acetates; HClO4-SiO2; 1.3-diol;

D O I：

10.1016/j.tetlet.2006.03.133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

HClO4-SiO2 has been used successfully for the deprotection of benzylidene acetals and the direct conversion of benzylidene acetals to the corresponding di-O-acetates. The reactions are very fast and yields are excellent. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3653 / 3658

页数：6

共 28 条

[1] N-pentenyl glycoside methodology in the stereoselective construction of the tetrasaccharyl cap portion of Leishmania lipophosphoglycan [J].

Arasappan, A ;

FraserReid, B .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2401-2406

[2] PHYSICAL STUDIES ON OLIGOSACCHARIDES RELATED TO SUCROSE .I. NMR STUDIES ON PERACETATES OF SUCROSE 1-KESTOSE AND NYSTOSE [J].

BINKLEY, WW ;

HORTON, D ;

BHACCA, NS .

CARBOHYDRATE RESEARCH, 1969, 10 (02) :245-&

[3]

Bollenback G. N., 1963, METHODS CARBOHYDRATE, V2, P326

[4] AN EASY PREPARATION OF 2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOPYRANOSIDES AND ALPHA-L-RHAMNOPYRANOSIDES [J].

CAMPOSVALDES, MT ;

MARINOALBERNAS, JR ;

VEREZBENCOMO, V .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1987, 6 (03) :509-513

[5]

CONCHIE J, 1963, METHODS CARBOHYDRATE, V2, P332

[6]

DENNISON JC, 1951, J CHEM SOC, P1616

[7] SOME ASPECTS OF REGIOSELECTIVE, STEREOSELECTIVE, AND CHEMOSELECTIVE REACTIONS IN CARBOHYDRATE-CHEMISTRY [J].

GAREGG, PJ .

PURE AND APPLIED CHEMISTRY, 1984, 56 (07) :845-858

[8]

GAREGG PJ, 1982, CARBOHYD RES, V108, P97

[9]

Greene T. W., 1999, PROTECTIVE GROUPS OR

[10]

Hanessian S., 1997, PREPARATIVE CARBOHYD, P53

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