phenyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-galactopyranoside
• CAS No.: 139608-14-3
• Molecular Formula: C₆₇H₆₂O₁₃S
• Molecular Weight: 1107.29
• Mol file: 139608-14-3.mol

Synonyms:phenyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-galactopyranoside

There total 5 articles about phenyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-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:

phenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside (139608-11-0) + 1-Methylethenyl 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranoside (139684-66-5) → phenyl 2,3,4-tri-O-benzoyl-6-O-<(2-methyl-4-oxo)-2-pentyl>-1-thio-β-D-galactopyranoside (139608-12-1) + phenyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-galactopyranoside (139608-14-3) + phenyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-galactopyranoside (139608-13-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In acetonitrile; at -25 ℃; for 0.5h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00042a010

Reference yield:

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose (80300-30-7) → phenyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-galactopyranoside (139608-14-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) titanocene dichloride, 2.) pyridine / 1.) toluene, 2.) THF, toluene, RT, 15 min

2: 4 A powdered molecular sieves, TMSOTf / acetonitrile / 0.5 h / -25 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; titanocene dichloride; In acetonitrile;

DOI:10.1021/ja00042a010

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → phenyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-thio-β-D-galactopyranoside (139608-14-3)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N, 4-DMAP / dimethylformamide / 6 h / 70 °C

2: pyridine / acetonitrile / Ambient temperature

3: TsOH / methanol / 2 h / Ambient temperature

4: 4 A powdered molecular sieves, TMSOTf / acetonitrile / 0.5 h / -25 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; toluene-4-sulfonic acid; triethylamine; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00042a010

upstream raw materials:

phenyl 2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside

1-Methylethenyl 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranoside

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

1-thiophenyl-β-D-galactopyranoside