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

Base Information

• Chemical Name: benzyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranoside)uronate
• CAS No.: 1448429-75-1
• Molecular Formula: C₅₀H₅₄O₁₁
• Molecular Weight: 830.972
• Mol file: 1448429-75-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about benzyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranoside)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: 90.0%

benzyl (3,4-di-O-benzyl-2-O-levulinoyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranoside)uronate (1448429-74-0) → benzyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranoside)uronate (1448429-75-1)

Guidance literature:

With hydrazine hydrate; In pyridine; acetic acid; at 0 - 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/ejoc.201300180

Reference yield:

β-D-galactose peracetate (4163-60-4) → benzyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranoside)uronate (1448429-75-1)

Guidance literature:

Multi-step reaction with 9 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 / 20 °C / Microwave irradiation; Inert atmosphere

8.2: 1 h / -10 °C / Inert atmosphere

9.1: hydrazine hydrate / pyridine; acetic acid / 1.5 h / 0 - 20 °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; hydrazine hydrate; acetic acid; In pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1002/ejoc.201300180

Reference yield:

allyl 2,3-di-Ο-benzyl-β-D-galactopyranoside (97817-99-7) → benzyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranoside)uronate (1448429-75-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 1 h / 20 °C

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

3.1: dichloromethane / 1 h / 20 °C / Microwave irradiation; Inert atmosphere

3.2: 1 h / -10 °C / Inert atmosphere

4.1: hydrazine hydrate / pyridine; acetic acid / 1.5 h / 0 - 20 °C / Inert atmosphere

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; potassium hydrogencarbonate; hydrazine hydrate; In pyridine; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201300180

upstream raw materials:

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

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

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

β-D-galactose peracetate

Downstream raw materials:

benzyl (4-O-benzyl-3-O-para-methoxybenzyl-2-O-levulinoyl-α-L-rhamnopyranosyl)-(1→2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate

(4-O-benzyl-2-O-levulinoyl-3-O-p-methoxybenzyl-β-L-rhamnopyranosyl)(trichloroacetyl)amine