Reaction of methyl 4,6-O-benzylidene-3-C-methyl-2-O-p-tolylsulfonyl-α-d

Add time:08/07/2019    Source:sciencedirect.com

Treatment of methyl 4,6-O-benzylidene-3-C-methyl-2-O-p-tolylsulfonyl-α-d-allopyranoside (1) with an excess of sodium methoxide in dry methyl sulfoxide gave a complex mixture from which four crystalline compounds have been isolated: methyl 4,6-O-benzylidene-3-C-methyl-α-d-allopyranoside (2) and its 3-O-methyl (3), 2,3-di-O-methyl (4), and 2-O-methyl (5) derivatives. Compound3 was converted into 6-deoxy-3-C-methyl-O-methyl-d-allose (2-hydroxy-d-cladinose,8) by a route which involved opening of the benzylidene ring by N-bromosuccinimide.

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