Cyclizations of Dialdehydes with Nitromethane. XV. Synthesis of Four Stereoisomeric Deoxynitroinositol Monomethyl Ethers

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Abstract
Methylation of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (1) followed by hydrolysis of the 5,6-ketal group and periodate oxidation gave 1,2-O-isopropylidene-3-O-methyl-α-L-xylo-pentodialdo-1,4-furanose (4). Addition of nitromethane to 4 afforded a mixture of 6-deoxy-1,2-O-isopropylidene-3-O-methyl-6-nitro-α-D-glucofuranose (5) and -β-L-idofuranose (6). Removal of the 1,2-ketal group led to a mixture of 6-deoxy-3-O-methyl-6-nitro-D-glucose (7) and -L-idose (8) from which the crystalline β-anomer of 7 could be isolated. Cyclization of the nitro hexoses by internal Henry reaction furnished four stereoisomeric deoxynitroinositol monomethyl ethers which were obtained in crystalline condition, in part directly and in part via acetone and acetyl derivatives. The scyllo (9), DL-myo-1 (10), muco-3 (14), and epi-3 (16) configurations were assigned to the products by n.m.r. spectroscopy.

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