2,3,4,6-Tetra-O-benzylgalactopyranosyl phenyl sulfoxide

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-benzylgalactopyranosyl phenyl sulfoxide
• CAS No.: 117307-18-3
• Molecular Formula: C40H40 O6 S
• Molecular Weight: 648.82
• DSSTox Substance ID: DTXSID50922389
• Nikkaji Number: J2.671.047B
• Mol file: 117307-18-3.mol

Synonyms:2,3,4,6-TBGOS;2,3,4,6-tetra-O-benzyl-beta-D-galactopyranosyl phenyl sulfoxide;2,3,4,6-tetra-O-benzylgalactopyranosyl phenyl sulfoxide

Chemical Property of 2,3,4,6-Tetra-O-benzylgalactopyranosyl phenyl sulfoxide

Chemical Property:

• Vapor Pressure: 3.63E-23mmHg at 25°C
• Boiling Point: 777.6°Cat760mmHg
• Flash Point: 424.1°C
• PSA: 82.43000
• Density: 1.26g/cm³
• LogP: 8.35780
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 15
• Exact Mass: 648.25456017
• Heavy Atom Count: 47
• Complexity: 872

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(C(C(C(O2)S(=O)C3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)S(=O)C3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5)OCC6=CC=CC=C6

Technology Process of 2,3,4,6-Tetra-O-benzylgalactopyranosyl phenyl sulfoxide

There total 6 articles about 2,3,4,6-Tetra-O-benzylgalactopyranosyl phenyl sulfoxide 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: 87.0%

phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside (74801-29-9) → phenyl (2,3,4,6-tetra-O-benzyl)-1-thio-β-D-galactopyranoside S-oxide (117307-18-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -30 ℃; for 0.333333h;

DOI:10.1071/CH01156

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → phenyl (2,3,4,6-tetra-O-benzyl)-1-thio-β-D-galactopyranoside S-oxide (117307-18-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / NaH / dimethylformamide / 0 - 40 °C

2: 87 percent / m-CPBA / CH₂Cl₂ / 0.33 h / -30 °C

With sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;

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-benzyl)-1-thio-β-D-galactopyranoside S-oxide (117307-18-3)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 87 percent / NaH / dimethylformamide / 0 - 40 °C

3: 87 percent / m-CPBA / CH₂Cl₂ / 0.33 h / -30 °C

With sodium methylate; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1071/CH01156

upstream raw materials:

phenyl-2,3,4,6-tetra-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

benzyl bromide

Downstream raw materials:

Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside

Benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside