2-(trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside
• CAS No.: 151072-05-8
• Molecular Formula: C₂₇H₃₃ClO₈Si
• Molecular Weight: 549.093
• Mol file: 151072-05-8.mol

Synonyms:2-(trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside

There total 7 articles about 2-(trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-chloroacetyl-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: 86.0%

2-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside (146934-37-4) + Chloroacetic anhydride (541-88-8) → 2-(trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside (151072-05-8)

Guidance literature:

With pyridine; at 0 ℃; for 0.166667h;

DOI:10.1016/0008-6215(83)85006-X

Reference yield:

benzoyl chloride (98-88-4) → 2-(trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside (151072-05-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / pyridine / 1 h / 0 - 25 °C

2: 89 percent / AcOH, H₂O / 80 °C

3: 82 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 0.25 h

4: 86 percent / pyridine / 0.17 h / 0 °C

With pyridine; (1S)-10-camphorsulfonic acid; water; acetic acid; In dichloromethane;

DOI:10.1016/0008-6215(83)85006-X

Reference yield:

2-(Trimethylsilyl)ethyl α-L-rhamnopyranoside (146934-36-3) → 2-(trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside (151072-05-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / 10-camphorsulfonic acid / 1 h / 25 °C

2: 91 percent / pyridine / 1 h / 0 - 25 °C

3: 89 percent / AcOH, H₂O / 80 °C

4: 82 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 0.25 h

5: 86 percent / pyridine / 0.17 h / 0 °C

With pyridine; (1S)-10-camphorsulfonic acid; water; acetic acid; In dichloromethane;

DOI:10.1016/0008-6215(83)85006-X

upstream raw materials:

2-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside

Chloroacetic anhydride

benzoyl chloride

2-(Trimethylsilyl)ethyl α-L-rhamnopyranoside

Downstream raw materials:

2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl chloride