Methyl 2-acetamido-6-bromo-3-O-<2',4'-di-O-benzoyl-3'-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl>-2,6-dideoxy-β-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2-acetamido-6-bromo-3-O-<2',4'-di-O-benzoyl-3'-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl>-2,6-dideoxy-β-D-glucopyranoside
• CAS No.: 149827-57-6
• Molecular Formula: C₄₁H₅₀BrNO₁₈
• Molecular Weight: 924.748
• Mol file: 149827-57-6.mol

Synonyms:Methyl 2-acetamido-6-bromo-3-O-<2',4'-di-O-benzoyl-3'-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl>-2,6-dideoxy-β-D-glucopyranoside

Chemical Property of Methyl 2-acetamido-6-bromo-3-O-<2',4'-di-O-benzoyl-3'-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl>-2,6-dideoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 2-acetamido-6-bromo-3-O-<2',4'-di-O-benzoyl-3'-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl>-2,6-dideoxy-β-D-glucopyranoside

There total 4 articles about Methyl 2-acetamido-6-bromo-3-O-<2',4'-di-O-benzoyl-3'-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl>-2,6-dideoxy-β-D-glucopyranoside 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: 55.0%

Methyl 2-acetamido-3-O-<2',4'-di-O-benzoyl-3'-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl>-2-deoxy-β-D-glucopyranoside (149827-56-5) → Methyl 2-acetamido-6-bromo-3-O-<2',4'-di-O-benzoyl-3'-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl>-2,6-dideoxy-β-D-glucopyranoside (149827-57-6)

Guidance literature:

With pyridine; 1H-imidazole; carbon tetrabromide; triphenylphosphine; In acetonitrile; for 22h; Ambient temperature;

DOI:10.1139/v93-076

Reference yield:

ethyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside (135303-37-6) → Methyl 2-acetamido-6-bromo-3-O-<2',4'-di-O-benzoyl-3'-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl>-2,6-dideoxy-β-D-glucopyranoside (149827-57-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) activated MS 4 Angstroem, AgOTf / 1) CH₂Cl₂, r.t., 2 h, 2) CH₂Cl₂, -75 deg C to -50 deg C, 2 h, then -50 deg C, 0.5 h

2: 71 percent / activated MS 4 Angstroem, N-iodosuccinimide, triflic acid / CH₂Cl₂ / 2 h / Ambient temperature

3: 78 percent / 60percent acetic acid / 1 h / 100 °C

4: 55 percent / imidazole, PPh₃, CBr₄, pyridine / acetonitrile / 22 h / Ambient temperature

With pyridine; 1H-imidazole; N-iodo-succinimide; carbon tetrabromide; trifluorormethanesulfonic acid; MS 4 Angstroem; silver trifluoromethanesulfonate; acetic acid; triphenylphosphine; In dichloromethane; acetonitrile;

DOI:10.1139/v93-076

Reference yield:

Ethyl 3-O-(2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside (149827-54-3) → Methyl 2-acetamido-6-bromo-3-O-<2',4'-di-O-benzoyl-3'-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl>-2,6-dideoxy-β-D-glucopyranoside (149827-57-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / activated MS 4 Angstroem, N-iodosuccinimide, triflic acid / CH₂Cl₂ / 2 h / Ambient temperature

2: 78 percent / 60percent acetic acid / 1 h / 100 °C

3: 55 percent / imidazole, PPh₃, CBr₄, pyridine / acetonitrile / 22 h / Ambient temperature

With pyridine; 1H-imidazole; N-iodo-succinimide; carbon tetrabromide; trifluorormethanesulfonic acid; MS 4 Angstroem; acetic acid; triphenylphosphine; In dichloromethane; acetonitrile;

DOI:10.1139/v93-076

upstream raw materials:

Methyl 2-acetamido-3-O-<2',4'-di-O-benzoyl-3'-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl>-2-deoxy-β-D-glucopyranoside

ethyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

Ethyl 3-O-(2',3',4'-tri-O-acetyl-α-L-rhamnopyranosyl)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

C₄₁H₅₁NO₁₈