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US 5,175,267 AGranted
Stereoselective glycosylation of hetercyclic bases
AssigneeUniversity of Georgia Research Foundation, Inc.
InventorChung K. Chu
Life of this patent
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Abstract
A method of preparation of 2',3'-dideoxy and 2',3'-dideoxy-2',3'-didehydronucleosides that includes the step of condensing a 1-O-activated-2-(aromatic or aliphatic)-selenenyl-5-O-protected ribose with a protected heterocyclic base in the presence of trimethylsilyl triflate or a Lewis acid to form a .beta.-anomeric nucleoside in high yield.
Claims10
A method for the stereoselective glycosylation of heterocyclic bases, comprising the steps of:
- i) providing 5-O-protected-3,4-dihydro-2(5H)-furanone;
- ii) reacting 5-O-protected-3,4-dihydro-2-(5H)-furanone with a strong base and silyl halide to produce the corresponding 1-silyl enol ether;
- iii) reacting the 1-silyl enol ether with a compound selected from the group consisting of an aromatic selenenyl halide and a C.sub.1 to C.sub.25 aliphatic selenenyl halide to produce a 5-O-protected-3,4-dihydro-3-.alpha.-(aromatic or aliphatic)-selenenyl-2(H)-furanone;
- iv) reducing the furanone to a furanose;
- v) activating the 1 position of the furanose by replacing the 1-OH group with a moiety selected from the group consisting of halide, O-acyl, and O-alkyl;
- and
- vi) condensing the activated furanose with a protected heterocyclic base.
4 more elements
Dependencies are inferred from the claim text.