phenyl (2,3,4,6-tetra-O-pivaloyl)-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl (2,3,4,6-tetra-O-pivaloyl)-1-thio-β-D-galactopyranoside
• CAS No.: 117606-53-8
• Molecular Formula: C₃₂H₄₈O₉S
• Molecular Weight: 608.794
• Mol file: 117606-53-8.mol

Synonyms:phenyl (2,3,4,6-tetra-O-pivaloyl)-1-thio-β-D-galactopyranoside

Chemical Property of phenyl (2,3,4,6-tetra-O-pivaloyl)-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl (2,3,4,6-tetra-O-pivaloyl)-1-thio-β-D-galactopyranoside

There total 4 articles about phenyl (2,3,4,6-tetra-O-pivaloyl)-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: 84.0%

1-thiophenyl-β-D-galactopyranoside (16758-34-2) + pivaloyl chloride (3282-30-2) → phenyl (2,3,4,6-tetra-O-pivaloyl)-1-thio-β-D-galactopyranoside (117606-53-8)

Guidance literature:

With dmap; In pyridine; at 100 ℃;

DOI:10.1071/CH01156

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 (2,3,4,6-tetra-O-pivaloyl)-1-thio-β-D-galactopyranoside (117606-53-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / NaOMe / methanol / 2 h / 20 °C

2: 84 percent / 4-dimethylaminopyridine / pyridine / 100 °C

With dmap; sodium methylate; In pyridine; methanol;

DOI:10.1071/CH01156

Reference yield:

thiophenol (108-98-5) → phenyl (2,3,4,6-tetra-O-pivaloyl)-1-thio-β-D-galactopyranoside (117606-53-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 49 percent / BF₃*Et₂O / CH₂Cl₂ / 5.5 h / Heating

2: 91 percent / NaOMe / methanol / 2 h / 20 °C

3: 84 percent / 4-dimethylaminopyridine / pyridine / 100 °C

With dmap; boron trifluoride diethyl etherate; sodium methylate; In pyridine; methanol; dichloromethane;

DOI:10.1071/CH01156

upstream raw materials:

1-thiophenyl-β-D-galactopyranoside

pivaloyl chloride

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

thiophenol

Downstream raw materials:

2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6R)-2-benzenesulfinyl-3,5-bis-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester

2,6-dimethylphenyl 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranoside

4-[(2S,3R,4S,5R,6R)-3,4,5-Tris-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-2-yloxy]-benzoic acid butyl ester

phenyl (2,3,4,6-tetra-O-pivaloyl)-1-thio-β-D-galactopyranoside S-oxide