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

Base Information

• Chemical Name: phenyl 2,3,4-tri-O-benzoyl-6-O-benzyl-1-thio-β-D-galactopyranoside
• CAS No.: 175978-00-4
• Molecular Formula: C₄₀H₃₄O₈S
• Molecular Weight: 674.771
• Mol file: 175978-00-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about phenyl 2,3,4-tri-O-benzoyl-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: 97.0%

benzoyl chloride (98-88-4) + phenyl 2,3-di-O-benzoyl-6-O-benzyl-1-thio-β-D-galactopyranoside (246513-03-1) → phenyl 2,3,4-tri-O-benzoyl-6-O-benzyl-1-thio-β-D-galactopyranoside (175978-00-4)

Guidance literature:

With pyridine; at 20 ℃; for 2h;

DOI:10.1080/07328309908544034

Reference yield: 84.0%

benzoyl chloride (98-88-4) + phenyl 6-O-benzyl-1-thio-β-D-galactopyranoside (175977-99-8) → phenyl 2,3,4-tri-O-benzoyl-6-O-benzyl-1-thio-β-D-galactopyranoside (175978-00-4)

Guidance literature:

With pyridine; for 8h; Ambient temperature;

DOI:10.1016/0008-6215(95)00353-3

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → phenyl 2,3,4-tri-O-benzoyl-6-O-benzyl-1-thio-β-D-galactopyranoside (175978-00-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / p-TsOH*H₂O / acetonitrile / 4 h / 20 °C

2: 97 percent / pyridine / 2 h / 20 °C

3: 84 percent / NaBH₃CN; HCl / tetrahydrofuran; diethyl ether / 0.17 h

4: 97 percent / pyridine / 2 h / 20 °C

With pyridine; hydrogenchloride; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; acetonitrile; 1: Cyclization / 2: Acylation / 3: Ring cleavage / 4: Acylation;

DOI:10.1080/07328309908544034

upstream raw materials:

benzoyl chloride

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

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

1-thiophenyl-β-D-galactopyranoside

Downstream raw materials:

2,3,4-tri-O-benzoyl-6-O-benzyl-α-D-galactopyranosyl bromide

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

O-(2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-D-glucopyranosyl azide

phenyl 2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside