methyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1-3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1-3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 502698-50-2
• Molecular Formula: C₄₄H₅₉NO₁₇
• Molecular Weight: 873.949
• Mol file: 502698-50-2.mol

Synonyms:methyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1-3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Chemical Property of methyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1-3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-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-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

There total 1 articles about methyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1-3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-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: 80.0%

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (122089-71-8) + methyl (2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside (441777-56-6) → methyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1-3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-α-L-rhamnopyranoside (502698-50-2) + methyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1-3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-β-L-rhamnopyranoside

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In diethyl ether; at -78 - 0 ℃; for 5h;

DOI:10.1016/S0957-4166(02)00580-3

Reference yield: 95.0%

methyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1-3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-α-L-rhamnopyranoside (502698-50-2) → methyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1-3)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-α-L-rhamnopyranoside (502698-52-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1.25h;

DOI:10.1016/S0957-4166(02)00580-3

Reference yield:

methyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1-3)-(2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-α-L-rhamnopyranoside (502698-50-2) → methyl α-L-rhamnopyranosyl-(1-3)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-α-L-rhamnopyranoside (502698-53-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / 50 percent aq. TFA / CH₂Cl₂ / 1.25 h / 0 °C

2: 98 percent / MeONa / methanol; CH₂Cl₂ / 20 °C / pH 10

With sodium methylate; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1016/S0957-4166(02)00580-3

upstream raw materials:

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate

methyl (2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Downstream raw materials:

methyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1-3)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

methyl α-L-rhamnopyranosyl-(1-3)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-2)-3,4-di-O-benzyl-α-L-rhamnopyranoside