1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Base Information

• Chemical Name: 1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside
• CAS No.: 146934-40-9
• Molecular Formula: C₄₇H₅₁ClO₁₄Si
• Molecular Weight: 903.452
• Mol file: 146934-40-9.mol

Synonyms:1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Chemical Property of 1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

There total 10 articles about 1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-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: 64.0%

2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl chloride (146934-39-6) + 2-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside (146934-37-4) → 1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside (146934-40-9)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; for 1h; -40 deg C to r.t.;

DOI:10.1016/S0040-4020(01)88331-9

Reference yield:

benzoyl chloride (98-88-4) → 1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside (146934-40-9)

Guidance literature:

Multi-step reaction with 4 steps

2: 91 percent / pyridine / dimethylformamide / 0.08 h / -45 °C

3: 84 percent / Cl₂ / CH₂Cl₂; CCl₄ / 0.17 h / 0 °C

4: 64 percent / CF₃SO₃Ag, 2,6-di-tert-butyl-4-methylpyridine, 4A molecular sieves / CH₂Cl₂ / 1 h / -40 deg C to r.t.

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; chlorine; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)88331-9

Reference yield:

methyl 1-thio-α-L-rhamnopyranoside (115678-08-5) → 1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside (146934-40-9)

Guidance literature:

Multi-step reaction with 4 steps

2: 91 percent / pyridine / dimethylformamide / 0.08 h / -45 °C

3: 84 percent / Cl₂ / CH₂Cl₂; CCl₄ / 0.17 h / 0 °C

4: 64 percent / CF₃SO₃Ag, 2,6-di-tert-butyl-4-methylpyridine, 4A molecular sieves / CH₂Cl₂ / 1 h / -40 deg C to r.t.

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; chlorine; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)88331-9

upstream raw materials:

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

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

benzoyl chloride

methyl 1-thio-α-L-rhamnopyranoside

Downstream raw materials:

1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside