Complete Sets of Monosubstituted γ-Cyclodextrins as Precursors for Further Synthesis

被引：13

作者：

Blahova, Marketa ^{[1
]}

Bednarova, Eva ^{[1
]}

Rezanka, Michal ^{[1
]}

Jindrich, Jindrich ^{[1
]}

机构：

[1] Charles Univ Prague, Dept Organ Chem, Fac Sci, Prague 12843 2, Czech Republic

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 02期

关键词：

BETA-CYCLODEXTRIN; CROSS-METATHESIS; DERIVATIVES; ALPHA; CATALYSIS; BROMIDE;

D O I：

10.1021/jo301656p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective alkylation of gamma-cyclodextrin with allyl or propargyl bromide, using optimized reaction conditions, followed by peracetylation of the remaining hydroxyl groups and separation of isomers resulted in the set of peracetylated 2(I)-O-, 3(I)-O- and 6(I)-O-alkylated cyclodextrins in up to 19% yields. Ozonolysis or oxidative cleavage of peracetylated allyl derivatives resulted in a complete set of peracetylated 2(I)-O, 3(I)-O-, and 6(I)-O-formylmethyl or -carboxymethyl derivatives. All of these derivatives are useful precursors for further preparation of regioselectively monosubstituted derivatives of gamma-cyclodextrin.

引用

页码：697 / 701

页数：5

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