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BoraneBu2BOTf: A mild reagent for the regioselective reductive ring opening of benzylidene acetals in carbohydrates

โœ Scribed by Lu Jiang; Tak-Hang Chan


Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
216 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


BH./Bu20T f is an effective reagent to reductively cleave 4,6-O-benzylidene acetals of various hexopyranosides to the corresponding 4-O-benzyl ethers. 4,6-O-Isopropylidene acetals can be similarly cleaved. Common protecting groups are stable to the reaction conditions.


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Ring-opening b-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 r