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

Base Information

Chemical Name:phenyl 2,6-di-O-benzoyl-4-O-chloroacetyl-3-deoxy-1-thio-β-D-ribo-hexoside
CAS No.:849132-43-0
Molecular Formula:C₂₈H₂₅ClO₇S
Molecular Weight:541.021
Hs Code.:

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

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

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

There total 9 articles about phenyl 2,6-di-O-benzoyl-4-O-chloroacetyl-3-deoxy-1-thio-β-D-ribo-hexoside 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: 72.0%

: 79-11-8
chloroacetic acid

: 849132-42-9
phenyl 2,6-di-O-benzoyl-3-deoxy-1-thio-β-D-xylo-hexopyranoside

: 849132-43-0
phenyl 2,6-di-O-benzoyl-4-O-chloroacetyl-3-deoxy-1-thio-β-D-ribo-hexoside

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In toluene; at 20 ℃; for 3h;
DOI:10.1016/j.tetasy.2004.12.004

Reference yield:

: 16758-34-2
1-thiophenyl-β-D-galactopyranoside

: 849132-43-0
phenyl 2,6-di-O-benzoyl-4-O-chloroacetyl-3-deoxy-1-thio-β-D-ribo-hexoside

Guidance literature:: Multi-step reaction with 8 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

With pyridine; methanol; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; water; tri-n-butyl-tin hydride; acetic acid; acetyl chloride; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In dichloromethane; chloroform; toluene; 8.1: Mitsunobu reaction;
DOI:10.1016/j.tetasy.2004.12.004

Reference yield:

: 98-88-4
benzoyl chloride

: 849132-43-0
phenyl 2,6-di-O-benzoyl-4-O-chloroacetyl-3-deoxy-1-thio-β-D-ribo-hexoside

Guidance literature:: Multi-step reaction with 7 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

With pyridine; methanol; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride; acetic acid; acetyl chloride; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In dichloromethane; chloroform; toluene; 7.1: Mitsunobu reaction;
DOI:10.1016/j.tetasy.2004.12.004