Multiple and regioselective introduction of protected sulfates into carbohydrates using sulfuryl imidazolium salts

The Journal of Organic Chemistry
Ahmed Desoky, Scott D Taylor

Abstract

Selective incorporation of trichloroethyl (TCE)-protected sulfates into monosaccharides was examined using reagent 2. In general, sulfation of 4,6-O-benzylidene acetals of galactosides and glucosides (2-OH versus 3-OH sulfations) proceeded in good to excellent yield and selectivity. Sulfation occurred predominantly at the 2-OH in 4,6-O-benzylidene acetals of alpha-glucosides and at the 3-OH in 4,6-O-benzylidene acetals of beta-galactosides and beta-glucosides. Good yields and selectivity was also achieved for the 3-OH in 3,4-diols of glucosides and galactosides. A glucoside bearing a 2-amino moiety and 6-OH group gave mainly the N-sulfated product in good yield. Selective sulfation of the primary 6-OH in galactose and glucose derivatives bearing one or two free secondary hydroxyl groups was also achieved usually in good yield and selectivity. Reagent 2 was also effective for the direct disulfation of diols of glucosides and galactosides, and trisulfated monosaccharides could be prepared from the disulfated compounds.

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Citations

Oct 17, 2014·Organic Letters·Vikram A Sarpe, Suvarn S Kulkarni
Jan 21, 2014·Chemical Communications : Chem Comm·Danny Geerdink, Adriaan J Minnaard
Feb 12, 2019·Chemical Society Reviews·Hannah E CaputoMark W Grinstaff
Mar 3, 2020·Organic & Biomolecular Chemistry·Santanu Jana, Suvarn S Kulkarni
Jul 26, 2011·Chemistry : a European Journal·Gopinath TiruchinapallyXuefei Huang
Dec 7, 2018·Chemical Reviews·Victoria Dimakos, Mark S Taylor
Jan 9, 2019·The Journal of Organic Chemistry·Daniel GorelikMark S Taylor

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