Allyl 2-O-benzoyl-3-O-[2,4-di-O-benzoyl-3,6-dideoxy-4-O-(p-methoxybenzyl)-α-D-arabino-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside

Base Information

• Chemical Name: Allyl 2-O-benzoyl-3-O-[2,4-di-O-benzoyl-3,6-dideoxy-4-O-(p-methoxybenzyl)-α-D-arabino-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside
• CAS No.: 182167-86-8
• Molecular Formula: C₅₂H₅₄O₁₄
• Molecular Weight: 902.992
• Mol file: 182167-86-8.mol

Synonyms:Allyl 2-O-benzoyl-3-O-[2,4-di-O-benzoyl-3,6-dideoxy-4-O-(p-methoxybenzyl)-α-D-arabino-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside

Chemical Property of Allyl 2-O-benzoyl-3-O-[2,4-di-O-benzoyl-3,6-dideoxy-4-O-(p-methoxybenzyl)-α-D-arabino-hexopyranosyl]-4,6-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-O-benzoyl-3-O-[2,4-di-O-benzoyl-3,6-dideoxy-4-O-(p-methoxybenzyl)-α-D-arabino-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside

There total 18 articles about Allyl 2-O-benzoyl-3-O-[2,4-di-O-benzoyl-3,6-dideoxy-4-O-(p-methoxybenzyl)-α-D-arabino-hexopyranosyl]-4,6-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: 93.0%

Benzoic acid (2S,3S,4S,5S,6R)-2-allyloxy-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester (182167-85-7) + ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-β-D-arabino-hexopyranoside (182167-82-4) → Allyl 2-O-benzoyl-3-O-[2,4-di-O-benzoyl-3,6-dideoxy-4-O-(p-methoxybenzyl)-α-D-arabino-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside (182167-86-8)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; 1,2-dichloro-ethane; at -30 ℃; for 0.25h;

DOI:10.1080/07328309608005684

Reference yield: 93.0%

Benzoic acid (2S,3S,4S,5S,6R)-2-allyloxy-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester (182167-85-7) + ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside (182167-81-3) → Allyl 2-O-benzoyl-3-O-[2,4-di-O-benzoyl-3,6-dideoxy-4-O-(p-methoxybenzyl)-α-D-arabino-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside (182167-86-8)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; 1,2-dichloro-ethane; at -30 ℃; for 0.25h;

DOI:10.1080/07328309608005684

Reference yield:

benzoyl chloride (98-88-4) → Allyl 2-O-benzoyl-3-O-[2,4-di-O-benzoyl-3,6-dideoxy-4-O-(p-methoxybenzyl)-α-D-arabino-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside (182167-86-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / pyridine / 1 h / Ambient temperature

2: 84 percent / H₂SO₄ / 0.75 h / 0 °C

3: SnCl₄ / CH₂Cl₂ / 2 h / Ambient temperature

4: 93 percent / NIS, TfOH / 1,2-dichloro-ethane; diethyl ether / 0.25 h / -30 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; sulfuric acid; tin(IV) chloride; In diethyl ether; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1080/07328309608005684

upstream raw materials:

Benzoic acid (2S,3S,4S,5S,6R)-2-allyloxy-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester

ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-β-D-arabino-hexopyranoside

ethyl 2,4-di-O-benzoyl-3,6-dideoxy-1-thio-α-D-arabino-hexopyranoside

Methyl 2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranoside

Downstream raw materials:

Allyl 2-O-benzoyl-3-O-(2,4-di-O-benzoyl-3,6-dideoxy-α-D-arabino-hexopyranosyl)-α-D-mannopyranoside