260779-96-2

Upstream product

• 40052-13-9 mono-tert-butyl malonate 
• 39483-51-7 ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside 

Downstream Products

• 260779-99-5 ethyl 2,3,4-tri-O-benzyl-6-O-[(2-O-benzoyl-6-O-benzyl-1-phenylthio-β-D-glucopyranos-3-yloxy)carbonylethanoyl]-1-thio-α-D-mannopyranoside 
• 260779-98-4 ethyl 2,3,4-tri-O-benzyl-6-O-[(2-O-benzoyl-4,6-O-benzylidene-1-phenylthio-β-D-glucopyranos-3-yloxy)carbonylethanoyl]-1-thio-α-D-mannopyranoside 
• 260780-00-5 phenyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-1-thio-β-D-glucopyranoside 3,6'-malonate 
• 262605-32-3 ethyl 2,3,4-tri-O-benzyl-6-O-[(2-O-benzoyl-1,6-di-O-benzyl-α-D-glucopyranos-3-yloxy)-carbonylethanoyl]-1-thio-α-D-mannopyranoside 
• 262605-37-8 benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-malonate 
• 262605-38-9 benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-malonate 
• 220009-59-6 benzyl 6-O-benzyl-2-deoxy-3-O-[3-(ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranosid-6-O-yl)-1,3-dioxopropyl]-2-phthalimido-α-D-glucopyranoside 
• 220009-66-5 benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside 3,6'-malonate 
• 173725-99-0 benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-succinate 
• 173726-00-6 benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-succinate 
• 260779-97-3 ethyl 2,3,4-tri-O-benzyl-6-O-(hydroxycarbonylethanoyl)-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

Prearranged glycosides, 9. - Chemical synthesis of a tetrasaccharide fragment related to the exopolysaccharide of Arthrobacter sp. CE-17

The tetrasaccharide 5-aminopentyl glycoside β-D-Manp-(1→4)-β-D-Glcp- (1→4)-α-L-Rhap-(1→3)-β-D-Glcp-1-O-(CH2)5NH2(22) related to the exopolysaccharide of Arthrobacter sp. CE-17 was synthesized by coupling of the properly protected disaccharide blocks β-D-Manp-(1→4)-β-D-Glcp-1-S-Ph (11) and α-L-Rhap-(1→3)-β-D-Glcp-1-O-(CH2)5NHZ (20). Building block 11 was obtained by intramolecular β-mannosylation of a malonyl-tethered disaccharide glycoside which was prepared from phenyl 4,6-O-benzylidene-1- thio-β-D-glucopyranoside (1) and ethyl 2,3,4-tri-O-benzyl-1-thio-α-D- mannopyranoside (5) in 5 steps. Building block 20 was obtained by coupling N- Z-protected 5-aminopentyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (14) obtained from the non-benzylated counterpart 12 with ethyl 2,3-di-O- benzoyl-4-O-chloroacetyl-1-thio-α-L-rhamnopyrano- side (18) obtained in 3 steps from ethyl 2,3-O-isopropylidene- 1-thio-α-L-rhamnopyranoside (15).

Synthesis of 4-O-D-mannopyranosyl-α-D-glucopyranosides by intramolecular glycosylation of 6-O-tethered mannosyl donors

A series of mannosyl donors linked via position 6 by a carbonate, oxalate, malonate, succinate, and phthalate tether, respectively, to position 3 of a glucoside and glucosamine acceptor afforded during intramolecular glycosylation, anomeric mixture of the corresponding disaccharides. The dependence of the diastereoselectivity on the glycosylation procedure, the solvent, and the blocking groups in comparison to an intermolecular mannosylation is studied. (C) 2000 Elsevier Science Ltd.