1976 Volume 40 Issue 8 Pages 1621-1624
Sequential oxidation and reduction of aryl 4, 6-O-benzylidene-β-D-glucosides with dimethyl sulfoxide-phosphorus pentoxide mixture (DMSO-P2O5) and sodium borohydride were carried out as a new means for the preparation of aryl β-D-mannopyranoside derivatives. p-Nitrophenyl 4, 6-O-benzylidene-β-D-mannopyranoside was obtained in 22% yield from the corresponding glucoside 3-O-acetate, whereas from the unprotected acetal, 4, 6-O-benzylidene acetals of the corresponding mannoside and alloside were isolated in the yields of 6.7 and 2.1%, respectively. Similarly, phenyl 4, 6-O-benzylidene β-D-mannoside, alloside, and altroside were obtained from the corresponding glucoside in 2.2, 0.8 and 2.1% yields, respectively.
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