3-deoxy-3-c-lower alkyl glycosides and nucleosides
Abstract
Abstract NOVEL 3 - DEOXY - 3 - C-LOWER-ALKYL-B-D-XYLOFURANOSYL HALIDE INTERMEDIATES ARE PREPARED BY THE STEPS OF (A) FORMING THE 5-O-TRITYL DERIVATIVE OF AN ALKYL 2,3-ANHYDROB-D-RIBOFURANOSIDE, (B) REACTING WITH A LOWER ALKYL GRIGNARD REAGENT TO OBTAIN THE ALKYL 3-DEOXY-3-C-LOWER ALKYL - 5 - O-TRITYL-B-D-XYLOFURANOSIDE, (C) REMOVAL OF 5 - 0 - TRITYL GROUP, (D) ACYLATING TO THE ALKYL 2,5-DI0 - ACYL - 3 - DEOXY-3-C-LOWER-ALKYL-B-D-XYLOFURANOSIDE, AND (E) CONVERTING THE LATTER COMPOUND TO THE 2,5-DI-OACYL-3-DEOXY-3-LOWER-ALKYL-D-XYLOFURANOSYL HALIDE BY A HALOGEN REPLACEMENT REACTION. STEPS C AND D MAY BE REVERSED. THE NOVEL INTERMEDIATE IS THEN CONVERTED INTO NOVEL PURINE AND PYRIMIDINE NUCLEOSIDES. THE NOVEL COMPOUNDS OF THIS INVENTION HAVE UTILITY IN VITRO IN INHIBITING CELL GROWTH. THEY ARE ALSO USEFUL AS SCREENING AGENTS FOR ULTRAVIOLET LIGHT.
Inventors
- 👤 Edward Walton
Bibliographic Details
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