Catalyst-Controlled, Site-Selective Sulfamoylation of Carbohydrate Derivatives,Organic Letters

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Catalyst-Controlled, Site-Selective Sulfamoylation of Carbohydrate Derivatives
Organic Letters ( IF 4.9 ) Pub Date : 2022-06-21 , DOI: 10.1021/acs.orglett.2c01590
Daniel J Gorelik ₁ , Julia A Turner ₁ , Mark S Taylor ₁

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Methods for site-selective sulfamoylation of secondary hydroxyl groups in pyranosides are described. Using a boronic acid catalyst, selective installation of a Boc-protected sulfamoyl group at the equatorial position of cis-diols in manno- and galacto-configured substrates has been achieved. Activation of trans-diol groups in gluco- and galacto-configured substrates is also possible by employing an organotin catalyst.

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