Method of synthesis of 1,3-dioxolane nucleosides

Details Method of synthesis of 1,3-dioxolane nucleosides Method of synthesis of 1,3-dioxolane nucleosides

1991-12-06

1994-01-04

Tsang, Cecilia

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

544225, 544229, 544262, 544265, 544276, 544277, 544310, 544313, 544314, 549214, C07D23902, C07D40704

Patent

active

052761517

ABSTRACT:
A synthesis of 1,3-dioxolane nucleosides that includes condensing a 2-0-protected-5-0-acylated-1,3-dioxolane with a purine or pyrimidine base in the presence of a titanium containing Lewis acid to provide predominately the desired .beta.-isomer in the C1'-position of a 1,3-dioxolane nucleoside.
A process for the resolution of a racemic mixture of 1,3-dioxolane nucleoside enantiomers is also disclosed that includes the step of exposing the racemic mixture to an enzyme that preferentially catalyzes a reaction in one of the enantiomers.

REFERENCES:
patent: 5041449 (1991-08-01), Belleau et al.
patent: 5047407 (1991-09-01), Belleau et al.
Bartlett, J. Am. Chem. Soc. 1983, 105, 2088-2089.
Annunziata et al, Tetrahedron Lett. vol. 31, No. 46, pp. 6733-6736 (1990).
Willson et al, Tetrahedron Lett. vol. 31, No. 13, pp. 1815-1818 (1990).
Choi, W., et al., "In Situ Complexation Directs the Stereochemistry of N-Glycosylation in the Synthesis of Oxathiolanyl and Dioxolanyl Nucleoside Analogues," J. Amer. Chem. Soc., 113(24) (1991) 9377-9379.
Evans, D. A., et al., "New Procedure for the Direct Generation of Titanium Enolates, Diastereoselective Bond Constructions with Representative Electrophiles," J. Amer. Chem. Soc., 112 (1990) 8215-8216.

Affiliated with

Also associated with

Rating

Method of synthesis of 1,3-dioxolane nucleosides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method of synthesis of 1,3-dioxolane nucleosides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of synthesis of 1,3-dioxolane nucleosides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-308404