82159-70-4

Upstream product

• 56543-17-0 methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside 
• 3013-58-9 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside 
• 3013-58-9 methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Regioselectivity in the ring opening of 2-phenyl-1,3-dioxan-2-yl radicals derived from cyclic benzylidene acetals and comparison with deoxygenation of a carbohydrate diol via its cyclic thionocarbonate

Ring-opening β-scission of monocyclic 2-phenyl-1,3-dioxan-2-yl radicals gives preferentially the more stabilised alkyl radical. However, analogous bicyclic radicals derived from two 4,6-O-benzylidene glucopyranosides afford primary radicals in preference to secondary radicals, a result that can be rationalised with the aid of DFT calculations. The report by Barton and Subramanian, that the opposite regioselectivity results from the tin hydride mediated reductive ring-opening of a corresponding glucosidic thionocarbonate, is shown to be in error.

STEREOSELETIVITIES IN THE REACTIONS OF α-D-HEXOPYRANOSID-4-ULOSES WITH DIAZOMETHANE

The stetreoselectivities in the reactions of diazomethane with various α-D-hexopyranosid-4-uloses are compared with those in Grignard reactions.The results support the hypothesis that the stereoselectivity of the diazomethane reaction is mainly controlled