A GENERAL-METHOD FOR THE SYNTHESIS OF CYCLODEXTRINYL ALDEHYDES AND CARBOXYLIC-ACIDS

被引：50

作者：

YOON, J ^{[1
]}

HONG, S ^{[1
]}

MARTIN, KA ^{[1
]}

CZARNIK, AW ^{[1
]}

机构：

[1] OHIO STATE UNIV,DEPT CHEM,COLUMBUS,OH 43210

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 09期

关键词：

D O I：

10.1021/jo00114a030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selective synthesis of the primary-side monoaldehyde of beta-cyclodextrin, 6-deoxy-6-formyl-beta-cyclodextrin, was accomplished by oxidation of the corresponding tosylate utilizing the Nace reaction (DMSO/collidine). This monoaldehyde was then used as the starting material in several reactions including reduction, addition of NaHSO3, addition of the alpha-nucleophiles hydroxylamine and hydrazine, and reductive amination. Of particular interest is the conversion of the monoaldehyde to the primary side carboxylic acid, 6-deoxy-6-carboxy-beta-cyclodextrin, via bromine oxidation. This general method sequence can be applied to any tosyl derivative of cyclodextrin as demonstrated in the synthesis of beta-cyclodextrin-A,D-dialdehyde and beta-cyclodextrin-A,D-diacid.

引用

页码：2792 / 2795

页数：4

共 36 条

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[2]

Bender M. L., 1978, CYCLODEXTRIN CHEM, DOI [10.1007/978-3-642-66842-5, DOI 10.1007/978-3-642-66842-5]

[3]

Bertagnini C., 1853, LIEBIGS ANN CHEM, V85, P268

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