Abstract
The reductive ring-opening reaction of benzylidene-protected glucosides and mannosides such as methyl 2,3-di- O-benzyl-4,6- O-benzylidene-α- d-glucoside ( 1) and methyl 2,3-di- O-benzyl-4,6- O-benzylidene-α- d-mannoside ( 4) by using a toluene stock solution of DIBAL-H and a dichloromethane stock solution of DIBAL-H gives mainly or selectively the corresponding 2,3,4-tri- O-benzyl derivatives ( 2, 5) and 2,3,6-tri- O-benzyl derivatives ( 3, 6), respectively, although that of methyl 2,3-di- O-benzyl-4,6- O-benzylidene-α- d-galactoside ( 7) gives methyl 2,3,6-tri- O-benzyl-α- d-galactoside ( 9) selectively irrespective of the solvent of the stock solution of DIBAL-H. Similarly, the reaction of the exo-isomer of methyl 2,3:4,6-di- O-benzylidene-α- d-mannopyranosides ( exo- 10) with a toluene stock solution and dichloromethane stock solutions of DIBAL-H selectively gives methyl 3- O-benzyl-4,6- O-benzylidene-α- d-mannoside ( 12) and methyl 2- O-benzyl-4,6- O-benzylidene-α- d-mannoside ( 11), respectively, although that of endo- 10 selectively affords 11, irrespective of the solvent of the stock solution of DIBAL-H.
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