phenyl 2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: phenyl 2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-1-thio-α-L-rhamnopyranoside
• CAS No.: 270075-67-7
• Molecular Formula: C₃₉H₅₅ClO₇S
• Molecular Weight: 703.38
• Mol file: 270075-67-7.mol

Synonyms:phenyl 2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-1-thio-α-L-rhamnopyranoside

Chemical Property of phenyl 2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-1-thio-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-1-thio-α-L-rhamnopyranoside

There total 7 articles about phenyl 2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-1-thio-α-L-rhamnopyranoside 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: 94.0%

Chloroacetic anhydride (541-88-8) + phenyl 2-O-benzoyl-4-O-stearoyl-1-thio-α-L-rhamnopyranoside (270075-66-6) → phenyl 2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-1-thio-α-L-rhamnopyranoside (270075-67-7)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0957-4166(99)00553-4

Reference yield:

phenyl 1-thio-α-L-rhamnopyranose (1214-98-8,105026-40-2,127061-11-4,131724-82-8) → phenyl 2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-1-thio-α-L-rhamnopyranoside (270075-67-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / scandium trifluoromethanesulfonate / acetone / 2 h / 23 °C

2: pyridine / CH₂Cl₂ / 0.25 h / 0 °C

3: aq. AcOH / 2 h / 50 °C

4: scandium trifluoromethanesulfonate / CH₂Cl₂ / 1 h / 23 °C

5: 90 percent aq. acetic acid / methanol / 8 h / 23 °C

6: 94 percent / C₅H₅N / CH₂Cl₂ / 1 h / 0 °C

With pyridine; acetic acid; scandium tris(trifluoromethanesulfonate); In methanol; dichloromethane; acetone; 1: Condensation / 2: Esterification / 3: Hydrolysis / 4: Etherification / 5: Hydrolysis / 6: Acylation;

DOI:10.1016/S0957-4166(99)00553-4

Reference yield:

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (131087-35-9) → phenyl 2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-1-thio-α-L-rhamnopyranoside (270075-67-7)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / CH₂Cl₂ / 0.25 h / 0 °C

2: aq. AcOH / 2 h / 50 °C

3: scandium trifluoromethanesulfonate / CH₂Cl₂ / 1 h / 23 °C

4: 90 percent aq. acetic acid / methanol / 8 h / 23 °C

5: 94 percent / C₅H₅N / CH₂Cl₂ / 1 h / 0 °C

With pyridine; acetic acid; scandium tris(trifluoromethanesulfonate); In methanol; dichloromethane; 1: Esterification / 2: Hydrolysis / 3: Etherification / 4: Hydrolysis / 5: Acylation;

DOI:10.1016/S0957-4166(99)00553-4

upstream raw materials:

Chloroacetic anhydride

phenyl 2-O-benzoyl-4-O-stearoyl-1-thio-α-L-rhamnopyranoside

phenyl 1-thio-α-L-rhamnopyranose

phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

5-(methoxycarbonyl)pentyl 2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-α-L-rhamnopyranoside

2-O-benzoyl-3-O-chloroacetyl-4-O-stearoyl-L-rhamnopyranosyl trichloroacetimidate