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

Base Information

• Chemical Name: Benzoic acid (2S,3S,4S,5S,6R)-2-allyloxy-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 182167-85-7
• Molecular Formula: C₃₂H₃₆O₉
• Molecular Weight: 564.632
• Mol file: 182167-85-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about Benzoic acid (2S,3S,4S,5S,6R)-2-allyloxy-4-hydroxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester 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: 83.0%

(2S,3S,4R,5S,6R)-2-Allyloxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3,4-diol (182167-84-6) + orthobenzoic acid trimethyl ester (707-07-3) → 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)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; for 0.5h; Ambient temperature;

DOI:10.1080/07328309608005684

Reference yield:

allyl 2,3-O-isopropylidene-α-D-mannopyranoside (85207-16-5) → 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)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / NaH / dimethylformamide / 2 h / Ambient temperature

2: 82 percent / 80percent aq. AcOH / 0.75 h / 60 °C

3: 83 percent / p-TsOH*H₂O / acetonitrile / 0.5 h / Ambient temperature

With sodium hydride; toluene-4-sulfonic acid; acetic acid; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/07328309608005684

Reference yield:

p-methoxybenzyl chloride (824-94-2) → 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)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / NaH / dimethylformamide / 2 h / Ambient temperature

2: 82 percent / 80percent aq. AcOH / 0.75 h / 60 °C

3: 83 percent / p-TsOH*H₂O / acetonitrile / 0.5 h / Ambient temperature

With sodium hydride; toluene-4-sulfonic acid; acetic acid; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/07328309608005684

upstream raw materials:

(2S,3S,4R,5S,6R)-2-Allyloxy-5-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3,4-diol

orthobenzoic acid trimethyl ester

allyl 2,3-O-isopropylidene-α-D-mannopyranoside

p-methoxybenzyl chloride

Downstream raw materials:

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

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

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

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