Abstract
Dinitrogen tetraoxide was used to convert 2-acetamido-1,3,4,6-tetra- O-acetyl-2-deoxy-β- D-glucopyranose ( 1) in high yield into the syrupy N-nitroso derivative 2, and benzyl 2-acetamido-3,4,6-tri- O-acetyl-2-deoxy-β- D-glucopyranose ( 6) into the crystalline N-nitroso analog 7. The N-nitroso derivative 2 in acetonitrile underwent photolysis by pyrex-filtered, u.v. light to regenerate the starting acetamide 1 in high yield; spontaneous decomposition of 2 afforded β- D-glucopyranose pentaacetate ( 3) and other products. In ethereal solution, compound 2 reacted with potassium hydroxide in isopropyl alcohol with loss of the 2-substituent and C-1, to give a C 5 acetylene, 1,2-dideoxy- D- erythro-pent-1-ynitol, isolated in high yield as its triacetate 4 and characterized by conversion into the known, crystalline 1,2-dideoxy-3- O-(3,5- dinitrobenzoyl)-4,5- O-isopropylidene- D- erythro-pent-1-ynitol ( 5).
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