219518-08-8

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 186665-14-5 ethyl 2-deoxy-<<(2,2,2-trichloroethoxy)carbonyl>amino>-1-thio-β-D-glucopyranoside 
• 144923-59-1 ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 

Downstream Products

• 219518-09-9 ethyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-<<(2,2,2-trichloroethoxy)carbonyl>amino>-1-thio-β-D-glucopyranoside 
• 1054630-79-3 ethyl 4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-3-O-(trifluoromethylsulfonyl)-1-thio-β-D-glucopyranoside 
• 1391598-04-1 ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-o-trifluoromethylbenzylideneamino-α-D-glucopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethyl)amino-1-thiol-β-D-glucopyranoside 
• 1391598-05-2 ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-o-trifluoromethylbenzylideneamino-β-D-glucopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-(2,2,2-trichloroethyl)amino-1-thiol-β-D-glucopyranoside 
• 1391598-06-3 ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-o-trifluoromethylbenzylideneamino-1-thiol-α-D-glucopyranoside 
• 219518-12-4 4-methoxyphenyl <3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-β-D-galactopyranosyl>-(1->4)-(6-O-benzyl-2-deoxy-2-(tetrachlorophthalimido)-β-D-glucopyranoside) 
• 219518-13-5 4-methoxyphenyl (3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-β-D-galactopyranosyl)-(1->4)-(2-acetamido-6-O-benzyl-2-deoxy-D-glucopyranoside) 
• 219518-11-3 ethyl 3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-1-thio-β-D-galactopyranoside 
• 219518-10-2 ethyl 3-O-acetyl-6-O-benzyl-2-deoxy-<<(2,2,2-trichloroethoxy)carbonyl>amino>-1-thio-β-D-glucopyranoside 
• 919078-15-2 2-{3-acetylamino-2-benzyloxy-6-benzyloxymethyl-5-[2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-tetrahydro-pyran-4-yloxy}-propionic acid 2-benzenesulfonyl-ethyl ester 
• 1053650-20-6 2-{3-[5-acetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-2-acetoxymethyl-5-acetylamino-6-benzyloxy-tetrahydro-pyran-4-yloxy}-propionic acid 2-benzenesulfonyl-ethyl ester 
• 919078-12-9 ethyl 4,6-O-benzylidene-2,3-dideoxy-3-iodo-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-allopyranoside 

Relevant academic research and scientific papers

Regioselective Glycosylation Strategies for the Synthesis of Group Ia and Ib Streptococcus Related Glycans Enable Elucidating Unique Conformations of the Capsular Polysaccharides

Group B Streptococcus serotypes Ia and Ib capsular polysaccharides are key targets for vaccine development. In spite of their immunospecifity these polysaccharides share high structural similarity. Both are composed of the same monosaccharide residues and

Synthesis of lactam and acetamido analogues of sialyl Lewis x tetrasaccharide and Lewis x trisaccharide

Virtually complete regioselective galactosylation of the diol acceptor p-methoxyphenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D- glucopyranoside (15) with the donors ethyl 3,4-di-O-acetyl-6-O-benzyl-2- deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1-thio-β-D- galactropyranoside (14), 4-methylphenyl 2,3-di-O-acetyl-4-azido-6-O-benzyl- 4-deoxy-1-thio-β-D-galactopyranoside (30), and 4-methylphenyl 2-O-acetyl-4- azido-6-O-benzyl-4-deoxy-3-O-(methoxyethanoyl)-1-thio-β-D-galactopyranoside (44) gave the lactose-diamine derivatives 16, 33, and 45, respectively. Fucosylation of the NHAc derivatives of 16 and 33 (17 and 34) with the donor 18 gave, after deprotection and N-acetylation, the 2-NHAc-Le(x) and 4-NHAc- Le(x) trisaccharides 3 and 5, respectively. Removal of the Troc group from the tetrasaccharide intermediate 23, followed by N-acetylation (→ 24), gave the NHAc-SLe(x) tetrasaccharide 2. Regioselective sialylation of the partially protected trisaccharide diols 21 and 37 with the sialyl donors 22 and 38 gave, after deprotection and lactamization, the SLe(x)-1'''→2'- lactam 1 and the SLe(x)-1'''→4'-lactam 4, respectively. The stannylidene acetal of the trisaccharide diol 21 was regioselectively 3-O-alkylated with tert-butyl bromoacetate; reductive removal of the Troc protecting group and addition of methanolic MeONa caused formation of a lactam ring. Compound 40 was thus obtained over four steps in an overall yield of 52%. Deprotection of 40 furnished the Le(x)-3,2-lactam 6 in 74% yield. Fucosylation of the lactose-diamine derivative 46 with donor 18 gave the N3-Le(x) trisaccharide derivative 47. The azido function of 47 was reduced with H2S, which caused spontaneous closure of a lactam ring. Removal of the protecting groups then gave the Le(x)-3,4-lactam 7. The total yields of 1, 2, 3, 4, 5, and 7 from the monosaccharide starting materials 14, 15, 18, 22, 30, 38, and 44 were 10%, 10%, 22%, 14%, 62%, and 28%, respectively.