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

Base Information

• Chemical Name: phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside
• CAS No.: 139608-36-9
• Molecular Formula: C₂₅H₂₈O₈S
• Molecular Weight: 488.559
• Mol file: 139608-36-9.mol

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

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

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about phenyl 2,3,4-tri-O-acetyl-6-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:

acetic anhydride (108-24-7) + phenyl 6-O-benzyl-1-thio-β-D-galactopyranoside (175977-99-8) → phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside (139608-36-9)

Guidance literature:

In pyridine; for 20h; Yield given;

DOI:10.1021/jo981203x

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside (139608-36-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / TsOH / acetonitrile / 2 h

2: BH₃NMe₃, AlCl₃ / tetrahydrofuran / 1 h / 60 °C

3: pyridine / 20 h

With aluminium trichloride; trimethylamine-borane; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; acetonitrile;

DOI:10.1021/jo981203x

Reference yield:

phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside (71676-30-7,87508-17-6,138922-03-9,87508-18-7) → phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside (139608-36-9)

Guidance literature:

Multi-step reaction with 2 steps

1: BH₃NMe₃, AlCl₃ / tetrahydrofuran / 1 h / 60 °C

2: pyridine / 20 h

With aluminium trichloride; trimethylamine-borane; In tetrahydrofuran; pyridine;

DOI:10.1021/jo981203x

upstream raw materials:

phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

acetic anhydride

phenyl 6-O-benzyl-1-thio-β-D-galactopyranoside

1-thiophenyl-β-D-galactopyranoside

Downstream raw materials:

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(5,6-dichloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

4-methoxyphenyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-(6-O-benzyl-2-deoxy-2-(tetrachlorophthalimido)-β-D-glucopyranoside)

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-6-benzyloxymethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl]-5,6-dichloro-isoindole-1,3-dione