allyl 2,6-di-O-benzyl-3,4-di-O-p-methoxybenzyl-α-D-mannopyranoside

Base Information

• Chemical Name: allyl 2,6-di-O-benzyl-3,4-di-O-p-methoxybenzyl-α-D-mannopyranoside
• CAS No.: 290811-10-8
• Molecular Formula: C₃₉H₄₄O₈
• Molecular Weight: 640.774
• Mol file: 290811-10-8.mol

Synonyms:allyl 2,6-di-O-benzyl-3,4-di-O-p-methoxybenzyl-α-D-mannopyranoside

Chemical Property of allyl 2,6-di-O-benzyl-3,4-di-O-p-methoxybenzyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2,6-di-O-benzyl-3,4-di-O-p-methoxybenzyl-α-D-mannopyranoside

There total 5 articles about allyl 2,6-di-O-benzyl-3,4-di-O-p-methoxybenzyl-α-D-mannopyranoside 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: 66.0%

p-methoxybenzyl chloride (824-94-2) + allyl 2,6-di-O-benzyl-α-D-mannopyranoside (290811-09-5) → allyl 2,6-di-O-benzyl-3,4-di-O-p-methoxybenzyl-α-D-mannopyranoside (290811-10-8)

Guidance literature:

allyl 2,6-di-O-benzyl-α-D-mannopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

p-methoxybenzyl chloride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 17h; Further stages.;

DOI:10.1039/b001386m

Reference yield:

D-Mannose (530-26-7) → allyl 2,6-di-O-benzyl-3,4-di-O-p-methoxybenzyl-α-D-mannopyranoside (290811-10-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 61 percent / acetyl chloride / 5 h / 50 - 60 °C

2.1: 78 percent / CSA / methanol / 10 h / Heating

3.1: NaH / dimethylformamide / 1 h / 0 °C

3.2: 88 percent / dimethylformamide / 15 h / 0 - 20 °C

4.1: 85 percent / aq. TFA / CH₂Cl₂ / 0.25 h

5.1: NaH / dimethylformamide / 0.5 h / 0 °C

5.2: 66 percent / dimethylformamide / 17 h / 0 - 20 °C

With camphor-10-sulfonic acid; sodium hydride; acetyl chloride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Condensation / 3.1: Metallation / 3.2: Etherification / 4.1: Hydrolysis / 5.1: Metallation / 5.2: Etherification;

DOI:10.1039/b001386m

Reference yield:

allyl α-D-mannopyranoside (41308-76-3,821794-45-0) → allyl 2,6-di-O-benzyl-3,4-di-O-p-methoxybenzyl-α-D-mannopyranoside (290811-10-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 78 percent / CSA / methanol / 10 h / Heating

2.1: NaH / dimethylformamide / 1 h / 0 °C

2.2: 88 percent / dimethylformamide / 15 h / 0 - 20 °C

3.1: 85 percent / aq. TFA / CH₂Cl₂ / 0.25 h

4.1: NaH / dimethylformamide / 0.5 h / 0 °C

4.2: 66 percent / dimethylformamide / 17 h / 0 - 20 °C

With camphor-10-sulfonic acid; sodium hydride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Condensation / 2.1: Metallation / 2.2: Etherification / 3.1: Hydrolysis / 4.1: Metallation / 4.2: Etherification;

DOI:10.1039/b001386m

upstream raw materials:

p-methoxybenzyl chloride

allyl 2,6-di-O-benzyl-α-D-mannopyranoside

D-Mannose

allyl α-D-mannopyranoside