174077-07-7

Upstream product

• 174077-03-3 Thexyldimethylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-β-D-xylo-4-hexulopyranoside 
• 174077-04-4 Thexyldimethylsilyl 2-azido-3,6-di-O-benzyl-2,4-dideoxy-4-C-methylene-β-D-xylohexopyranoside 
• 174077-10-2 Thexyldimethylsilyl 2-azido-3,6-di-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-xylo-4-hexulopyranoside 
• 174077-02-2 dimethylthexylsilyl 3,6-di-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside 
• 174077-01-1 Thexyldimethylsilyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 174077-11-3 Thexyldimethylsilyl 2-azido-3,6-di-O-(tert-butyldimethylsilyl)-2-deoxy-4-C-methylene-β-D-xylohex-4-ulopyranoside 
• 174077-09-9 Thexyldimethylsilyl 2-azido-3,6-di-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranoside 
• 157488-88-5 thexyldimethylsilyl 2-azido-2-deoxy-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 174077-05-5 Thexyldimethylsilyl 2-azido-3,6-di-O-benzyl-2,4-dideoxy-4-C-(hydroxymethyl)-β-D-galactopyranoside 
• 174077-17-9 Thexyldimethylsilyl 2-azido-3,6-di-O-benzyl-4-C-cyano-2,4-dideoxy-β-D-galactopyranoside 

Downstream Products

• 174077-08-8 Thexyldimethylsilyl 2-azido-3,6-di-O-benzyl-2,4-dideoxy-4-C-formyl-β-D-glucopyranoside 
• 174175-62-3 Thexyldimethylsilyl 4-C-<2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-3-<(R)-phenylsulfinyl>-D-talo-hept-2-enit-1-yl>-2-azido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside 
• 174077-18-0 Thexyldimethylsilyl 4-C-<2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-3-<(R)-phenylsulfinyl>-D-galacto-hept-2-enit-1-yl>-2-azido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside 
• 174175-63-4 Thexyldimethylsilyl 4-C-(1-O-acetyl-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-talo-hept-2-enit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside 
• 174077-19-1 Thexyldimethylsilyl 4-C-(1-O-acetyl-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-galacto-hept-2-enit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside 
• 174175-64-5 Thexyldimethylsilyl 4-C-(2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-talo-hept-2-enit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside 
• 174077-20-4 Thexyldimethylsilyl 4-C-(2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-galacto-hept-2-enit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside 
• 174175-65-6 Thexyldimethylsilyl 4-C-(2,6-anhydro-4,5,7-tri-O-benzyl-D-threo-L-galacto-heptit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside 
• 174077-21-5 Thexyldimethylsilyl 4-C-(2,6-anhydro-4,5,7-tri-O-benzyl-D-threo-L-talo-heptit-1-yl)-2-acetamido-3,6-di-O-benzyl-2,4-dideoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of Carbon-Bridged N-Acetyl-C-lactosamine and derivatives

4-C-Formyl-2-azidoglucopyranoside 12a, required for N-acetyl-C-lactosamine synthesis as electrophile, was obtained from thexyldimethylsilyl 2-azido-2-deoxy-glucopyranoside 3 via readily available 4-O-unprotected 6a and then 4-C-methylene derivative 8a in overall seven steps.Alternatively, regioselective silylation of 3 with tert-butyldimethylsilyl chloride gave 4-O-unprotected 6b which was transformed by a similar reaction sequence into 12a.In order to circumvent a Wittig reaction, 6a was transformed into triflate 13 the reaction of which with 4-C-cyano derivative 14 followed by reduction with DIBAH and base-catalyzed isomerization also afforded 12a.Reaction of 12a with 1-C-lithiated 2-phenylsulfinyl-D-galactal 15 as nucleophile furnished C-disaccharide intermediates 16a and 16b as diastereoisomers.Ensuing removal of the phenylsulfinyl group with Raney nickel and diastereospecific 2b-hydrogen and 3b-hydroxy transfer afforded β(1->4)-connected N-acetyl-C-lactosamines 19a and 19b; their structures were deduced from derivatives 20a, b and 21a, b on the basis of 1H-NMR data.Hydrogenolytic O-debenzylation of 19b afforded hydroxymethylene-bridged N-acetyl-C-lactosamine 2b'. - Keywords: C-Saccharide; C-Glycosides; C-Lactosamine; 1-Lithiogalactal; Vinillithium; Branched sugars; Glucosamine, C-formyl