methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
• CAS No.: 88337-87-5
• Molecular Formula: C₃₃H₃₈O₁₄
• Molecular Weight: 658.656
• Mol file: 88337-87-5.mol

Synonyms:methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Chemical Property of methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

There total 11 articles about methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-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: 93.0%

methyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside (88331-96-8) + 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide (5158-64-5) → methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside (88337-87-5)

Guidance literature:

With 4 A molecular sieve; mercury(II) cyanide; In dichloromethane; 1.) -80 deg C --> r.t., overnight;

DOI:10.1016/0008-6215(83)88465-1

Reference yield: 76.0%

ethyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside (125520-01-6) + methyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside (88331-96-8) → methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside (88337-87-5)

Guidance literature:

With molecular sieve; bromine; silver trifluoromethanesulfonate; In dichloromethane; for 0.75h;

DOI:10.1021/jo00296a055

Reference yield:

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose (7404-35-5,17081-04-8,20853-37-6,24332-95-4,27821-10-9,27821-11-0,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,30021-94-4) → methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside (88337-87-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 93.1 percent / aq. NH₃ / methanol / 6 h

2: 87.5 percent / DBU / CH₂Cl₂ / 5 h

3: TMSOTf / CH₂Cl₂ / 3 h / -25 - 20 °C

4: 4.29 g / pyridine / 20 °C

With pyridine; ammonium hydroxide; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane;

DOI:10.1081/CAR-120003740

upstream raw materials:

ethyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside

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

2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide

benzoyl chloride

Downstream raw materials:

methyl α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

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

isopropyl 2,4-di-O-benzoyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside