4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranosyl trichloroacetimidate
• CAS No.: 1312107-98-4
• Molecular Formula: C₃₃H₃₉Cl₃N₂O₁₇
• Molecular Weight: 842.035
• Mol file: 1312107-98-4.mol

Synonyms:4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranosyl trichloroacetimidate

Chemical Property of 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranosyl trichloroacetimidate

There total 14 articles about 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranosyl trichloroacetimidate 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:

4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranose (1312108-33-0) + trichloroacetonitrile (545-06-2) → 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranosyl trichloroacetimidate (1312107-98-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ol2013704

Reference yield:

allyl 4-O-(3-acetoxybenzoyl)-2,3-O-methylorthoacetyl-α-L-rhamnopyranoside (1312108-09-0) → 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranosyl trichloroacetimidate (1312107-98-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: water / tetrahydrofuran / 0.5 h / 21 °C

2.1: toluene / Distillation

2.2: 0.83 h / -78 - 21 °C / Inert atmosphere

3.1: ethylenediamine / butan-1-ol / 2 h / 85 °C

4.1: pyridine / 16 h / 21 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid / 0.5 h / 80 °C / Inert atmosphere

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylenediamine; In tetrahydrofuran; dichloromethane; toluene; butan-1-ol;

DOI:10.1021/ol2013704

Reference yield:

allyl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-α-L-rhamnopyranoside (1312108-00-1) → 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranosyl trichloroacetimidate (1312107-98-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene / Distillation

1.2: 0.83 h / -78 - 21 °C / Inert atmosphere

2.1: ethylenediamine / butan-1-ol / 2 h / 85 °C

3.1: pyridine / 16 h / 21 °C

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid / 0.5 h / 80 °C / Inert atmosphere

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylenediamine; In dichloromethane; toluene; butan-1-ol;

DOI:10.1021/ol2013704

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

allyl 4-O-(3-acetoxybenzoyl)-2,3-O-methylorthoacetyl-α-L-rhamnopyranoside

allyl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-α-L-rhamnopyranoside

allyl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

Downstream raw materials:

cholesteryl 4-O-(3-hydroxybenzoyl)-3-O-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

cholesteryl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl)-α-L-rhamnopyranoside