p-tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: p-tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
• CAS No.: 1354391-61-9
• Molecular Formula: C₃₄H₃₂O₆S
• Molecular Weight: 568.69

Synonyms:p-tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Chemical Property of p-tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of p-tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

There total 4 articles about p-tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

benzyl bromide (100-39-0) + benzoyl chloride (98-88-4) + p-methylphenyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside (220645-86-3) → p-tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (1354391-61-9)

Guidance literature:

p-methylphenyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside; With di(n-butyl)tin oxide; In toluene; for 6h; Reflux;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

benzoyl chloride; With triethylamine; In dichloromethane; at 20 ℃; for 2h; regioselective reaction;

DOI:10.1021/acs.orglett.7b03275

Reference yield:

benzoic acid anhydride (93-97-0) + p-methylphenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (220645-87-4) → p-tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (1354391-61-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/acs.joc.6b02745

Reference yield:

C33H42O5SSi → p-tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (1354391-61-9)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C

2: dmap; triethylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.joc.6b02745

upstream raw materials:

benzoic acid anhydride

p-methylphenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

benzyl bromide

benzoyl chloride

Downstream raw materials:

(2S,3R)-2'-O-benzoyl-3'-O-benzyl-4',6'-O-benzylidene-β-D-galactopyranosyl-(1'->1)-2-azido-3-O-benzyloctadecan-1,3-diol

C₇₂H₁₁₆N₂O₉

(2S,3R)-3-O-benzyl-4,6-O-benzylidene-2-O-carbamoyl-β-D-galactopyranosyl-(1'->1)-2-azido-3-O-benzyloctadecan-1,3-diol

(2S,3R)-3'-O-benzyl-4',6'-O-benzylidene-β-D-galactopyranosyl-(1'->1)-2-azido-3-O-benzyloctadecan-1,3-diol

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