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|Title:||Method and compositions for the synthesis of BCH-189 and related compounds|
|Abstract:||The present invention relates to a method of preparing BCH-189 and various analogs of BCH-189 from inexpensive precursors with the option of introducing functionality as needed. This synthetic route allows the stereoselective preparation of the biologically active isomer of these compounds, .beta.-BCH-189 and related compounds. Furthermore, the steochemistry at the nucleoside 4' position can be controlled to produce enantiomerically-enriched .beta.-BCH-189 and its analogs.|
|Inventor(s):||Liotta; Dennis C. (McDonough, GA), Choi; Woo-Baeg (North Brunswick, NY)|
|Assignee:||Emory University (Atlanta, GA)|
|Filing Date:||Jun 07, 1995|
|Claims:||1. A method of preparing a .beta.-1,3-oxathiolane pyrimidine nucleoside, comprising reacting a compound of the formula: ##STR8## wherein R' is an acyl group and R is an oxygen protecting group, with a pyrimidine base in the presence of SnCl, wherein the pyrimidine base had the formula: ##STR9## wherein X is a trialkylsilylamino group; Z is a trialkylsilyl group; and Y is fluoro. |
2. The method of claim 1, wherein the oxygen protecting group is a trialkylsilyl group or a t-butyldiphenylsilyl group.
3. The method of claim 1, wherein R' is an acetate.
4. The method of claim 2, wherein the trialkylsilyl group is trimethylsilyl .