methyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside
• CAS No.: 218279-58-4
• Molecular Formula: C₂₃H₂₃ClO₈
• Molecular Weight: 462.884
• Mol file: 218279-58-4.mol

Synonyms:methyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside

Chemical Property of methyl 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 methyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside

There total 1 articles about methyl 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: 89.0%

methyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside (88331-96-8) + Chloroacetic anhydride (541-88-8) → methyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside (218279-58-4)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; at -45 ℃; for 0.5h;

DOI:10.1016/S0008-6215(98)00216-X

Reference yield: 88.0%

methyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside (218279-58-4) → 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl chloride (146934-39-6)

Guidance literature:

With zinc chloride diethyl ether; Dichloromethyl methyl ether; In dichloromethane; 1,2-dichloro-ethane; at 65 ℃; for 7h;

DOI:10.1016/S0008-6215(98)00216-X

Reference yield:

methyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside (218279-58-4) → methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3-deoxy-α-D-xylo-hexopyranoside (218279-78-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 88 percent / α,α-dichloromethyl methyl ether, ZnCl2*Et2O / 1,2-dichloro-ethane; CH2Cl2 / 7 h / 65 °C

2: 84 percent / 2,6-di-tert-butyl-4-methylpyridine, silver trifluoromethanesulfonate / CH₂Cl₂ / -15 deg C, 30 min, then -> room temp., 2 h

3: 66 percent / α,α-dichloromethyl methyl ether, ZnCl2*Et2O / CH2Cl2 / 1.25 h / 60 °C

4: 80 percent / 2,6-di-tert-butyl-4-methylpyridine, AgOTf / CH₂Cl₂ / 1.5 h / -15 - 0 °C

5: 88 percent / thiourea, sym-collidine / CH₂Cl₂; methanol / 36 h / 25 °C

6: 69 percent / 2,6-di-tert-butyl-4-methylpyridine, AgOTf / CH₂Cl₂ / 1 h / 0 °C

7: 79 percent / triphenylphosphine / CH₂Cl₂ / 24 h / 35 °C

8: pyridine / Ambient temperature

9: hydrogen / 10percent Pd/C / acetic acid; ethanol

With pyridine; 2,4,6-trimethyl-pyridine; 2,6-di-tert-butyl-4-methylpyridine; zinc chloride diethyl ether; Dichloromethyl methyl ether; hydrogen; silver trifluoromethanesulfonate; thiourea; triphenylphosphine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/S0008-6215(98)00216-X

upstream raw materials:

methyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside

Chloroacetic anhydride

Downstream raw materials:

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

methyl (3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside

methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside

methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-3-fluoro-α-D-galactopyranoside