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US 5,476,924 AGranted
Protecting group for acetals and methods of using the same in the activation of saccharides
AssigneeDuke University
InventorsBertram O. Fraser-Reid, David R. Mootoo, J. Cristobal Lopez
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Abstract
The present invention relates to a method of protecting the hemiacetal or acetal group at the anomeric carbon of a saccharide molecule comprising forming a 4-alkenyl glycoside or 4-alkenoyl glycosyl ester. The invention also relates to use of 4-alkenyl glycosides and 4-alkenoyl glycosyl esters in carbohydrate chemistry, including in the synthesis of oligosaccharides.
Claims9
A method of synthesizing a complex sugar comprising:
- (i) reacting a cyclic reducing sugar with a 4-alkenyl alcohol so that a 4-alkenyl glycoside is formed;
- and
- (ii) reacting said 4-alkenyl glycoside with a halonium compound in the presence of a sugar alcohol so that a glycosidic bond is formed between said reducing sugar and said sugar alcohol.
A method of synthesizing a complex sugar comprising:
- (i) reacting a cyclic reducing sugar with 4-alkenoic acid so that a 1-(4-alkenoyl)glycosyl ester is formed;
- and
- (ii) reacting said glycosyl ester with a halonium compound in the presence of a sugar alcohol so that a glycosidic bond is formed between said reducing sugar and said sugar alcohol.
A method of synthesizing a complex sugar comprising:
- reacting a 1-(4-alkenoyl)glycosyl ester, wherein said glycosyl moiety is derived from a cyclic reducing sugar, with a halonium compound in the presence of a sugar alcohol so that said complex sugar is formed.
Dependencies are inferred from the claim text.