Abstract
The title compound (9) a new nitro sugar and potential starting-point for the synthesis of hitherto unknown stereoisomers in the deoxynitroinositol series, was prepared by a sequence of high-yielding reactions. Methyl 2.3-anhydro-4.6- O- benzylidene-α- D-mannopyranoside was converted into methyl 3- O-methyl-α- D-altropyranoside (3) by the action of sodium methoxide followed by debenzylidenation esssentially according to established procedures. Acetolysis of 3 and subsequent Zemple´n transesterification gave syrupy 3- O-methyl- D-altrose, from which the furanoid 1,2:5.6-di- O-isopropylidene and 1,2- O-isopropylidene (7) derivatives were prepared by standard acetonation and partial Hydrolysis Periodate oxidation of 7, and addition of nitromethane to the product. furnished crystalline 6-deoxy-1.2- O-isopropylidene-3- O-methyl-6-nitro-β- D-altrofuranose (8) as the chief epimer. Deacetonation of 8 by trifluoroacetic acid 9 in crystalline form.
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