Effective protection of the N-sulfate of glucosamine derivatives with the 2,2,2-trichloroethyl group |
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Authors: | Jianfang Chen |
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Institution: | State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China |
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Abstract: | The 2,2,2-trichloroethyl (TCE) group was utilized as the first protecting group for N-sulfates (chlorosulfuric acid TCE ester, Et3N, DMAP, DMF). Glycosylation with 3,4,6-tri-O-acetyl-N-trichloroethylsulfuryl-α-d-glucosaminosyl trichloroacetimidate provided the corresponding β-glucosaminosides stereoselectively and in excellent yields. The TCE protection stayed stable under a variety of conditions for the manipulation of other protecting groups, and was readily removable with zinc in the presence of ammonium chloride in methanol. |
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Keywords: | 2 2 2-Trichloroethyl (TCE) group N-Sulfate Glucosamine Protecting group Glycosylation |
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