126113-70-0

Upstream product

• 126092-07-7 phenyl 2,3:4,6-bis-O-isopropylidene-1-thio-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 316188-12-2 phenyl 6-O-[(tert-butyl)diphenylsilyl]-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside 
• 310870-40-7 phenyl 6-O-[(tert-butyl)diphenylsilyl]-1-thio-α-D-mannopyranoside 
• 126092-08-8 phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 316188-14-4 phenyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside 

Downstream Products

• 168138-16-7 phenyl 2,4,6-tri-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 220009-55-2 benzyl O-(2,4,6-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-bemzoyl-6-O-benzyl-α-D-glucopyranoside 3,3'-succinate 
• 220009-39-2 benzyl O-(2,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1-> 4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside 3,3'-succinate 
• 316188-15-5 phenyl 2,4,6-tri-O-benzyl-3-O-(3-carboxypropanoyl)-1-thio-α-D-mannopyranoside 
• 316188-19-9 benzyl 2-O-benzoyl-6-O-benzyl-3-O-[1,4-dioxo-4-(phenyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside-3-O-yl)butyl]-α-D-glucopyranoside 
• 316188-17-7 benzyl 2-O-benzoyl-4,6-O-benzylidene-3-O-[1,4-dioxo-4-(phenyl 2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside-3-O-yl)butyl]-α-D-glucopyranoside 

Relevant academic research and scientific papers

Facile construction of 1,2-cis glucosidic linkage using sequential oxidation-reduction route for synthesis of an ER processing α-glucosidase i substrate

The fluorescence-labeled hexasaccharide (Glcα1-2Glcα1- 3Glcα1-3Manα1-2Manα1-2Manα) was synthesized as a substrate for the processing enzyme α-glucosidase I. To construct the 1,2-cis glucosidic linkages, we employed an α stereoselective coupling using the mannosyl donor by assisted neighboring-group participation, followed by conversion of the stereochemistry of the C-2 hydroxyl group in the mannose residue using sequential oxidation of C-2 hydroxyl group to a 2-keto group and stereoselective reduction of the hydroxyl group to the gluco-configuration to provide the corresponding α-glucoside derivative. Using this strategy, the three consecutive α-glucosidic linkages were easily obtained in a stereoselective manner. Finally, the Dansyl labeled hexasaccharide derivative was used to measure the activity of processing α-glucosidase I.

Prearranged glycosides. Part 12. Intramolecular mannosylations of glucose derivatives via prearranged glycosides

A series of prearranged glycosides 5, 17, 23, 28, 37, and 41, having a benzyl-protected 1-thiomannosyl donor linked through its positions 2, 3, 4, and 6 via succinate and malonate tethers, respectively, to positions 2, 3, and 6 of a benzyl glucopyranoside acceptor, were prepared by condensation of the respective mannosyl succinates and malonates with suitably protected benzyl glucopyranosides. The prearranged glycosides were intramolecularly coupled under various conditions to give the corresponding tethered (1 → 4)-linked disaccharides. The yields and anomer ratios of the products of these couplings were interpreted in terms of the thermodynamic stability of the resulting disaccharides. In the case of prearranged glycoside 17, having positions 3 of both the donor and the acceptor linked by a succinate tether, a strong dependence of the diastereoselectivity of the intramolecular glycosylation on the activation procedure was observed. All other cases did not show a significant dependence of the outcome of the anomeric configuration in intramolecular glycosylation on the activation procedure or the solvent.