101024-13-9Relevant academic research and scientific papers
REACTION OF 1,6-ANHYDRO-4-O-BENZYL-2-DEOXY-2-ISOTHIOCYANATO-β-D-GLUCOYRANOSE; PREPARATION OF 2-AMINO-1,6-ANHYDRO-2,3-DIDEOXY-β-D-ribo-HEXOPYRANOSE
Elbert, Tomas,Cerny, Miloslav
, p. 2000 - 2009 (2007/10/02)
1,6-Anhydro-4-O-benzyl-2-deoxy-2-isothiocyanato-β-D-glucopyranose (IV), prepared from 2-amino-1,6-anhydro-4-O-benzyl-2-deoxy-β-D-glucopyranose (I) by reaction with carbon disulfide followed by oxidation with iodine, was converted into the 3-O-p-toluenesulfonate VII.This was cyclized to give either the 2,3-epimino derivative X or the thiazoline XII. 2-Acetamido-3-S-acetyl-1,6-anhydro-4-O-benzyl-2-deoxy-3-thio-β-D-glucopyranose (XVI), obtained from compound XII, was desulfurized with Raney nickel to afford 2-acetamido-1,6-anhydro-2,3-dideoxy-β-D-ribo-hexopyranose (XVII).The isothiocyanato group was not affected upon acetylation of compound IV and acetolysis of the 1,6-anhydride bond with acetic anhydride and trifluoroacetic acid.
