Dimethylboron bromide--interconversion of protecting groups: preparation of MTM [(methylthio) methyl] ethers, O, S-acetals, and cyanomethyl ethers

HE Morton, Y Guindon

Index: Morton, Howard E.; Guindon, Yvan Journal of Organic Chemistry, 1985 , vol. 50, # 25 p. 5379 - 5382

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Citation Number: 39

Abstract

The results in Table I1 are quite straightforward, and it is particularly gratifying to note that dimethyl acetals can be transformed into 0-methyl, S-alkyl, and 0-methyl S-phenyl acetals in good yield-(entries-1-3). 18 Under identical experimental conditions diethyl acetals work equally well (entries 4 and 5). Also, both a-and P-methyl glycosides are readily converted into the corresponding P-phenylthio glycosides in good yield (entries 6 and 7). 19 (14)(a) ...