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

Base Information

• Chemical Name: phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-galactopyranoside
• CAS No.: 146920-71-0
• Molecular Formula: C₂₅H₂₈O₈S
• Molecular Weight: 488.559
• Mol file: 146920-71-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about phenyl 2,4,6-tri-O-acetyl-3-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: 90.2%

acetic anhydride (108-24-7) + phenyl 3-O-benzyl-1-thio-β-D-galactopyranoside (196876-47-8) → phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-galactopyranoside (146920-71-0)

Guidance literature:

With pyridine; for 12h;

DOI:10.1081/CAR-100103955

Reference yield:

methyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-galactopyranoside (81348-24-5) → phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-galactopyranoside (146920-71-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / conc. H₂SO₄ / 6 h / Ambient temperature

2: Me₃SiOTf / CH₂Cl₂ / 15 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; sulfuric acid; In dichloromethane;

DOI:10.1016/0008-6215(92)85026-V

Reference yield:

phenylthiotrimethylsilane (4551-15-9) + 1,2,4,6-tetra-O-acetyl-3-O-benzyl-D-galactopyranose (127853-23-0) → phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-galactopyranoside (146920-71-0) + phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-α-D-galactopyranoside

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 15h; Ambient temperature;

DOI:10.1016/0008-6215(92)85026-V

upstream raw materials:

phenylthiotrimethylsilane

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

acetic anhydride

phenyl 3-O-benzyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

ethyl 6-(2,4,6-tri-O-acetyl-3-O-benzyl-β-D-galactopyranosyloxy)hexanoate