1442422-75-4

Upstream product

• 1379519-57-9 (2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-thia-α-D-mannopyranoside 
• 1361016-58-1 (2-methyl-5-tert-butylphenyl) 1-thio-α-D-mannopyranoside 
• 1442422-74-3 (2-methyl-5-tert-butylphenyl) 4,6-O-(p-methoxybenzylidene)-1-thia-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 7340-90-1 2-methyl-5-tert-butylthiophenol 

Downstream Products

• 1442422-58-3 (2-methyl-5-tert-butylphenyl) 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenyl-methyl)-7-S-tris(thiophenol)-l-glycero-1-thia-α-D-thiomannoheptopyranoside 
• 1442422-60-7 S-phenyl [(2-methyl-5-tert-butylphenyl) 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-α-D-mannoheptopyranosylurinate] 
• 1442422-61-8 methyl [(2-methyl-5-tertbutylphenyl)2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-a-D-mannoheptopyranosyl urinate] 
• 1442422-67-4 (2-methyl-5-tert-butylphenyl) 3-O-acetyl-2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-D-glycero-1,6-dithio-α-D-mannoheptopyranoside 
• 1442422-68-5 5-tert-butyloxycarbonylpentyl 3-O-acetyl-2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-D-glycero-1-thia-α-D-mannoheptopyranoside 
• 1442422-76-5 (2-methyl-5-tert-butylphenyl) 2-O-benzyl-7,8-dideoxy-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-D-glycero-1-thia-α-D-manno-oct-7-eno-pyranoside 
• 1442422-77-6 (2-methyl-5-tert-butylphenyl) 2-O-benzyl-7,8-dideoxy-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-α-D-manno-oct-7-eno-pyranoside 
• 1442422-78-7 (2-methyl-5-tert-butylphenyl) 3,6-anhydro-2,7-di-O-benzyl-4-O-(p-methoxybenzyl)-L-glycero-1-thia-α-D-mannoheptopyranoside 
• 1442422-57-2 (2-methyl-5-tert-butylphenyl) 2,7-di-O-benzyl-4-O-6-S-(1-cyano)benzylidene-D-glycero-1,6-dithio-α-D-mannohepto-pyranoside 
• 1442422-62-9 (2-methyl-5-tert-butylphenyl) 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-α-D-mannoheptopyranoside 
• 1442422-63-0 (2-methyl-5-tert-butylphenyl) 2,7-di-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-α-D-mannoheptopyranoside 
• 1442422-64-1 (2-methyl-5-tert-butylphenyl) 6-S-acetyl-2,7-di-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-D-glycero-1,6-dithio-α-D-mannoheptopyranoside 
• 1442422-65-2 (2-methyl-5-tert-butylphenyl) 6-S-acetyl-2,7-di-O-benzyl-3-O-(2-naphthalenylmethyl)-D-glycero-1,6-dithio-α-D-mannoheptopyranoside 
• 1442422-66-3 (2-methyl-5-tert-butylphenyl) 2,7-di-O-benzyl-4-O,6-S-(1-cyano)benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-1,6-dithio-α-D-mannoheptopyranoside 

Relevant academic research and scientific papers

Improved methods for the stereoselective synthesis of mannoheptosyl donors and their glycosides: Toward the synthesis of the trisaccharide repeating unit of the Campylobacter jejuni RM1221 capsular polysaccharide

In view of the importance of 6-deoxymannoheptosides as structural units in the Campylobacter jejuni RM1221 capsular polysaccharide, the development of effective synthetic protocols for 4-O-6-S-α-cyanobenzylidene thio-d-mannoheptapyranoside donors carrying either 3-O-naphthylmethyl or 3-O-acetyl groups is described starting from d-mannose. In particular, tris(phenylthio)methyllithium is found to undergo highly stereoselective addition to a mannose-6-aldehyde in sharp contrast to the vinyl Grignard reagent whose reactions were essentially devoid of selectivity. A brief survey of coupling reactions with the two donors indicted the 3-O-acetyl system to be highly α-selective whereas the 3-O-naphthylmethyl congener was highly β-selective indicating that the presence of the seventh carbon atom in these donors is not detrimental to coupling selectivity in either instance.