p-methoxyphenyl 2-O-allyl-3-O-benzyl-4,6-di-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: p-methoxyphenyl 2-O-allyl-3-O-benzyl-4,6-di-O-acetyl-β-D-glucopyranoside
• CAS No.: 1622258-18-7
• Molecular Formula: C₂₇H₃₂O₉
• Molecular Weight: 500.546
• Mol file: 1622258-18-7.mol

Synonyms:

Chemical Property of p-methoxyphenyl 2-O-allyl-3-O-benzyl-4,6-di-O-acetyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methoxyphenyl 2-O-allyl-3-O-benzyl-4,6-di-O-acetyl-β-D-glucopyranoside

There total 6 articles about p-methoxyphenyl 2-O-allyl-3-O-benzyl-4,6-di-O-acetyl-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:

4-methoxyphenyl β-D-glucopyranoside (3150-20-7,6032-32-2,28541-75-5,85481-53-4,89731-58-8,109121-56-4,121468-39-1,12167-34-9) → p-methoxyphenyl 2-O-allyl-3-O-benzyl-4,6-di-O-acetyl-β-D-glucopyranoside (1622258-18-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: camphorsulfonic acid / N,N-dimethyl-formamide / 8 h / 60 °C / 180.02 Torr / Inert atmosphere; Schlenk technique

2.1: di(n-butyl)tin oxide / methanol / 24 h / Inert atmosphere; Schlenk technique; Reflux

2.2: 72 h / 20 °C / Inert atmosphere; Schlenk technique

3.1: sodium hydride / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

4.1: acetic acid / dichloromethane; water / 48 h / 60 °C / Inert atmosphere; Schlenk technique

5.1: pyridine; dmap / 16 h / 20 °C / Inert atmosphere; Schlenk technique

With pyridine; dmap; sodium hydride; di(n-butyl)tin oxide; acetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201402260

Reference yield:

4-methoxyphenyl 4,6-di-O-benzylidene-β-D-glucopyranoside → p-methoxyphenyl 2-O-allyl-3-O-benzyl-4,6-di-O-acetyl-β-D-glucopyranoside (1622258-18-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: di(n-butyl)tin oxide / methanol / 24 h / Inert atmosphere; Schlenk technique; Reflux

1.2: 72 h / 20 °C / Inert atmosphere; Schlenk technique

2.1: sodium hydride / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

3.1: acetic acid / dichloromethane; water / 48 h / 60 °C / Inert atmosphere; Schlenk technique

4.1: pyridine; dmap / 16 h / 20 °C / Inert atmosphere; Schlenk technique

With pyridine; dmap; sodium hydride; di(n-butyl)tin oxide; acetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201402260

Reference yield:

p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6) → p-methoxyphenyl 2-O-allyl-3-O-benzyl-4,6-di-O-acetyl-β-D-glucopyranoside (1622258-18-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium methylate / methanol / 1.5 h / 20 °C / Inert atmosphere; Schlenk technique

2.1: camphorsulfonic acid / N,N-dimethyl-formamide / 8 h / 60 °C / 180.02 Torr / Inert atmosphere; Schlenk technique

3.1: di(n-butyl)tin oxide / methanol / 24 h / Inert atmosphere; Schlenk technique; Reflux

3.2: 72 h / 20 °C / Inert atmosphere; Schlenk technique

4.1: sodium hydride / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

5.1: acetic acid / dichloromethane; water / 48 h / 60 °C / Inert atmosphere; Schlenk technique

6.1: pyridine; dmap / 16 h / 20 °C / Inert atmosphere; Schlenk technique

With pyridine; dmap; sodium methylate; sodium hydride; di(n-butyl)tin oxide; acetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201402260

upstream raw materials:

C₂₃H₂₈O₇

acetic anhydride

p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

4-methoxyphenyl β-D-glucopyranoside

Downstream raw materials:

3-O-benzyl-4,6-di-O-acetyl-2-O-(2-iodoethyl)-α-D-glucopyranose

3-O-benzyl-4,6-di-O-acetyl-2-O-(2-iodoethyl)-β-D-glucopyranose