benzyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyroside)uronate

Base Information

• Chemical Name: benzyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyroside)uronate
• CAS No.: 1448429-69-3
• Molecular Formula: C₄₂H₄₈O₁₄
• Molecular Weight: 776.835
• Mol file: 1448429-69-3.mol

Synonyms:benzyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyroside)uronate

Chemical Property of benzyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyroside)uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyroside)uronate

There total 8 articles about benzyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyroside)uronate 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: 91.0%

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate (122089-71-8) + benzyl (allyl 2,3-di-O-benzyl-β-D-galactopyranoside)uronate (311797-10-1) → benzyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyroside)uronate (1448429-69-3)

Guidance literature:

2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate; benzyl (allyl 2,3-di-O-benzyl-β-D-galactopyranoside)uronate; In dichloromethane; at -40 - 20 ℃; for 1h; Microwave irradiation; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 ℃; for 1.25h; Inert atmosphere;

DOI:10.1002/ejoc.201300180

Reference yield:

β-D-galactose peracetate (4163-60-4) → benzyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyroside)uronate (1448429-69-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 24 h / 0 - 20 °C

2.1: sodium methylate / methanol / 18 h / 20 °C

3.1: (1S)-10-camphorsulfonic acid / acetonitrile / 2 h / 20 °C

4.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C

4.2: 2 h / 0 °C

5.1: acetic acid / water / 2 h / 80 °C

6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 1 h / 20 °C

7.1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 16 h / Inert atmosphere

8.1: dichloromethane / 1 h / -40 - 20 °C / Microwave irradiation; Inert atmosphere

8.2: 1.25 h / -40 °C / Inert atmosphere

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; sodium methylate; sodium hydride; potassium hydrogencarbonate; acetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1002/ejoc.201300180

Reference yield:

allyl β-D-galactopyranoside (2595-07-5,821794-45-0) → benzyl (2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyroside)uronate (1448429-69-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: (1S)-10-camphorsulfonic acid / acetonitrile / 2 h / 20 °C

2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C

2.2: 2 h / 0 °C

3.1: acetic acid / water / 2 h / 80 °C

4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 1 h / 20 °C

5.1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 16 h / Inert atmosphere

6.1: dichloromethane / 1 h / -40 - 20 °C / Microwave irradiation; Inert atmosphere

6.2: 1.25 h / -40 °C / Inert atmosphere

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; (1S)-10-camphorsulfonic acid; sodium hydride; potassium hydrogencarbonate; acetic acid; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1002/ejoc.201300180

upstream raw materials:

allyl 2,3-di-Ο-benzyl-β-D-galactopyranoside

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

benzyl (allyl 2,3-di-O-benzyl-β-D-galactopyranoside)uronate

allyl 2,3-di-O-benzyl-β-D-galactopyranosiduronic acid