A catalytic process for the chemo- and regioselective functionalization of nonprotected carbohydrates has been developed. This novel process allows selective thiocarbonylation, acylation, and sulfonylation of a particular hydroxy group in a particular carbohydrate in the simultaneous presence of structurally similar carbohydrates such as anomers. The utilization of Bu2SnCl2 enables direct thiocarbonylation of C(2)-OH in methyl a-D-glucopyranoside in the presence of its �-D-anomer with >99% yield and 97% chemoselectivity; moreover, no regioisomers are formed in this process. On the other hand, utilization of Me2SnCl2 leads to direct functionalization of C(6)-OH in methyl �-D-glucopyranoside in the presence of its a-D-anomer with 91% yield and 98% chemoselectivity; again, no regioisomers are formed in this process. Thus, the chemoselectivity can be switched by regulating only the length of the alkyl chain in the organotin catalyst.

Chemo- and regioselective functionalization of non-protected carbohydrates under practical conditions

245th National Meeting (2013)

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