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
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
收藏
页码:697 / 701
页数:5
相关论文
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