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

Base Information

• Chemical Name: allyl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-α-L-rhamnopyranoside
• CAS No.: 1312108-00-1
• Molecular Formula: C₂₀H₂₄O₉
• Molecular Weight: 408.405
• Mol file: 1312108-00-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about allyl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-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: 98.0%

allyl 4-O-(3-acetoxybenzoyl)-2,3-O-methylorthoacetyl-α-L-rhamnopyranoside (1312108-09-0) + acetic acid (64-19-7,77671-22-8) → allyl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-α-L-rhamnopyranoside (1312108-00-1)

Guidance literature:

With water; In tetrahydrofuran; at 21 ℃; for 0.5h; regioselective reaction;

DOI:10.1021/ol2013704

Reference yield:

allyl 2,3-O-methylorthoacetyl-α-L-rhamnopyranoside → allyl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-α-L-rhamnopyranoside (1312108-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dicyclohexyl-carbodiimide / dichloromethane / 0.5 h / 21 °C / Inert atmosphere

1.2: 3 h / 0 - 21 °C / Inert atmosphere

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

With water; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol2013704

Reference yield:

3-acetoxybenzoic acid (6304-89-8) → allyl 4-O-(3-acetoxybenzoyl)-2-O-acetyl-α-L-rhamnopyranoside (1312108-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 20 °C

2: tetrahydrofuran; water / 20 °C

With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/anie.201811403

upstream raw materials:

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

acetic acid

3-acetoxybenzoic acid

3-Carboxyphenol

Downstream raw materials:

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

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

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