175652-63-8

Upstream product

• 175652-49-0 ((2R,3R,4S,5R,6S)-2-[(acetyloxy)methyl]-6-{[(3aR,5R,6S,6aS)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-yl]sulfanyl}oxane-3,4,5-triyl triacetate) 
• 175652-62-7 1,2-O-isopropylidene-3-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-thio-α-D-glucofuranose 
• 55951-90-1 1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 
• 19879-84-6 tetraacetyl thioglucose 
• 108-24-7 acetic anhydride 

Relevant academic research and scientific papers

Synthesis of sulfur-linked analogues of nigerose, laminarabiose, laminaratriose, gentiobiose, gentiotriose, and laminaran trisaccharide Y

Sulfur-linked analogues of 3-O-α-D-glucopyranosyl-D-glucose (nigerose), 3-O-β-D-glucopyranosyl-D-glucose (laminarabiose), 6-O-β-D-glucopyranosyl-D-glucose (gentiobiose), O-β-D-glucopyranosyl-(1 → 3)-O-β-D-glucopyranosyl-(1 → 3)-D-glucose (laminaratriose), O-β-D-glucopyranosyl-(1 → 6)-O-β-D-glucopyranosyl-(1 → 6)-D-glucose (gentiotriose) and 3,6-di-O-β-D-glucopyranosyl-D-glucose (laminaran trisaccharide Y), namely, respectively, 3-thionigerose (6), 3-thiolaminarabiose (II), 6-thiogentiobiose (21), 3(I),3(II)-dithiolaminaratriose (16), 6(I),6(ii)-dithiogentiotriose (29) and 3(I),6(I)-dithiolaminaran trisaccharide Y (37) have been conveniently prepared by S(N)2 reactions of the corresponding anomer of D-glucopyranose 1-thiolate with suitably activated monosaccharide derivatives in N,N-dimethylformamide (for 6 and 21) or in tetrahydrofuran in the presence of a crown ether (for 11). A sequence involving the reaction of non-anomeric thiolates with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide was alternatively used for the preparation of 11 and 21 but proved less satisfactory. The preparation of thiotrisaccharides 16, 29, and 37 involved a mixed approach.