Action of boron trichloride on 1,4:3,6-dianhydro-D-glucitol

Add time:09/24/2019    Source:sciencedirect.com

Under mild conditions, 1,4:3,6-dianhydro-D-glucitol is converted by boron trichloride mainly into 1,6-dichloro-1,6-dideoxy-D-glucitol, isolated as the 2,4-O-benzylidene and 2,4:3,5-di-O-benzylidene derivatives. 2,4-O-Benzylidene-1,6-dichloro-1,6-dideoxy-D-glucitol is converted by sodium methoxide into 2,4-O-benzylidene-1-chloro-1-deoxy-6-O-methyl-D-glucitol, and by lithium aluminium hydride into 2,4-O-benzylidene-1,6-dideoxy-D-glucitol. The ready cleavage of tetrahydrofuran rings by boron trichloride endows them with potential value as novel blocking groups in carbohydrate chemistry.

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