The Methyl Ethers of 2-Amino-2,6-dideoxyglucopyranose (Quinovosamine)

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Abstract
The 3-, 4-, and 3,4-dimethyl ethers of 2-amino-2,6-dideoxyglucose have been synthesized. 3,4-Di-O-methyl-L-rhamnal on treatment with nitrosyl chloride gave dimeric 2-deoxy-3,4-di-O-methyl-2-nitroso-α-L-rhamnopyranosyl chloride which on reduction and N-acetylation afforded 2-acetamido-2,6-dideoxy-3,4-di-O-methyl-L-glucose and 2-acetamido-2,6-dideoxy-4-O-methyl-L-glucose. 2-Acetamido-2,6-dideoxy-3-O-methyl-D-glucose was made from methyl 2-acetamido-2-deoxy-3-O-methyl-α-D-glucopyranoside by the reduction of its 6-deoxy-6-iodo derivative, prepared from synthesized methyl 2-acetamido-4-O-acetyl-2-deoxy-3-O-methyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside, to yield the required 6-deoxy-L-glucose derivative.

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