phenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-galactopyranoside
• CAS No.: 911684-18-9
• Molecular Formula: C₃₀H₃₂O₇S
• Molecular Weight: 536.646
• Mol file: 911684-18-9.mol

Synonyms:phenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-galactopyranoside

There total 7 articles about phenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-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: 100.0%

acetic anhydride (108-24-7) + phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside (231623-55-5) → phenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-galactopyranoside (911684-18-9)

Guidance literature:

With pyridine; dmap; at 0 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2013.06.038

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → phenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-galactopyranoside (911684-18-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 56 percent / camphorsulfonic acid / acetonitrile / 4 h / 20 °C

2: 100 percent / sodium hydride / dimethylformamide / 20 °C

3: aq. HCl / acetone / 2 h / 70 °C

4: 120 mg / triethylamine; DMAP / CH₂Cl₂ / 2 h / 20 °C

With hydrogenchloride; dmap; camphor-10-sulfonic acid; sodium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/ja063247q

Reference yield:

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose (13992-16-0,23661-28-1,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1,24404-53-3) → phenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-galactopyranoside (911684-18-9)

Guidance literature:

Multi-step reaction with 5 steps

1: NaOMe / methanol / 2 h / 20 °C

2: 56 percent / camphorsulfonic acid / acetonitrile / 4 h / 20 °C

3: 100 percent / sodium hydride / dimethylformamide / 20 °C

4: aq. HCl / acetone / 2 h / 70 °C

5: 120 mg / triethylamine; DMAP / CH₂Cl₂ / 2 h / 20 °C

With hydrogenchloride; dmap; camphor-10-sulfonic acid; sodium methylate; sodium hydride; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/ja063247q

upstream raw materials:

acetic anhydride

phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside

1-thiophenyl-β-D-galactopyranoside

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose

Downstream raw materials:

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose

Benzoic acid (3aS,4R,6S,7R,7aS)-4-(1-methoxy-1-methyl-ethoxymethyl)-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

1-thiophenyl-β-D-galactopyranoside

phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside