phenyl 2,6-di-O-benzoyl-3-deoxy-1-thio-β-D-ribo-hexopyranoside

Base Information

• Chemical Name: phenyl 2,6-di-O-benzoyl-3-deoxy-1-thio-β-D-ribo-hexopyranoside
• CAS No.: 849132-44-1
• Molecular Formula: C₂₆H₂₄O₆S
• Molecular Weight: 464.539
• Mol file: 849132-44-1.mol

Synonyms:phenyl 2,6-di-O-benzoyl-3-deoxy-1-thio-β-D-ribo-hexopyranoside

Chemical Property of phenyl 2,6-di-O-benzoyl-3-deoxy-1-thio-β-D-ribo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,6-di-O-benzoyl-3-deoxy-1-thio-β-D-ribo-hexopyranoside

There total 10 articles about phenyl 2,6-di-O-benzoyl-3-deoxy-1-thio-β-D-ribo-hexopyranoside 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 2,6-di-O-benzoyl-4-O-chloroacetyl-3-deoxy-1-thio-β-D-ribo-hexoside (849132-43-0) → phenyl 2,6-di-O-benzoyl-3-deoxy-1-thio-β-D-ribo-hexopyranoside (849132-44-1)

Guidance literature:

With 2,6-dimethylpyridine; thiourea; In methanol; dichloromethane; at 35 ℃; for 12h;

DOI:10.1016/j.tetasy.2004.12.004

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → phenyl 2,6-di-O-benzoyl-3-deoxy-1-thio-β-D-ribo-hexopyranoside (849132-44-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: CSA

2.1: pyridine / CH₂Cl₂

3.1: AcOH; H₂O

4.1: trifluoroacetic acid / CHCl₃ / 0.08 h / 20 °C

4.2: 95 percent / H₂O / acetonitrile; CHCl₃ / 0.5 h / 20 °C

5.1: 79 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

6.1: 75 percent / tributylstannane; AIBN / toluene / 3 h / 60 °C

7.1: 74 percent / acetyl chloride; methanol / 24 h / 20 °C

8.1: 72 percent / Ph₃P; diethyl azodicarboxylate / toluene / 3 h / 20 °C

9.1: 87 percent / H₂NCSNH₂; 2,6-lutidine / methanol; CH₂Cl₂ / 12 h / 35 °C

With pyridine; 2,6-dimethylpyridine; methanol; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; water; tri-n-butyl-tin hydride; acetic acid; acetyl chloride; thiourea; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In methanol; dichloromethane; chloroform; toluene; 8.1: Mitsunobu reaction;

DOI:10.1016/j.tetasy.2004.12.004

Reference yield:

benzoyl chloride (98-88-4) → phenyl 2,6-di-O-benzoyl-3-deoxy-1-thio-β-D-ribo-hexopyranoside (849132-44-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridine / CH₂Cl₂

2.1: AcOH; H₂O

3.1: trifluoroacetic acid / CHCl₃ / 0.08 h / 20 °C

3.2: 95 percent / H₂O / acetonitrile; CHCl₃ / 0.5 h / 20 °C

4.1: 79 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

5.1: 75 percent / tributylstannane; AIBN / toluene / 3 h / 60 °C

6.1: 74 percent / acetyl chloride; methanol / 24 h / 20 °C

7.1: 72 percent / Ph₃P; diethyl azodicarboxylate / toluene / 3 h / 20 °C

8.1: 87 percent / H₂NCSNH₂; 2,6-lutidine / methanol; CH₂Cl₂ / 12 h / 35 °C

With pyridine; 2,6-dimethylpyridine; methanol; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; acetic acid; acetyl chloride; thiourea; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In methanol; dichloromethane; chloroform; toluene; 7.1: Mitsunobu reaction;

DOI:10.1016/j.tetasy.2004.12.004

upstream raw materials:

phenyl 2,6-di-O-benzoyl-4-O-chloroacetyl-3-deoxy-1-thio-β-D-ribo-hexoside

1-thiophenyl-β-D-galactopyranoside

benzoyl chloride

phenyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside