4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-methoxy-4-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-methoxy-4-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 109889-84-1
• Molecular Formula: C₂₈H₂₉BrO₁₁
• Molecular Weight: 621.436

Synonyms:

Chemical Property of 4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-methoxy-4-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-methoxy-4-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-tetrahydro-pyran-3-yl ester

There total 4 articles about 4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-methoxy-4-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-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:

(E)-3-(4-methoxyphenyl)propenoyl chloride (34446-64-5,42996-84-9) → 4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-methoxy-4-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-tetrahydro-pyran-3-yl ester (109889-84-1,116215-19-1,128796-76-9)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 4-dimethylaminopyridine

2: pyridine / 4-dimethylaminopyridine

3: 4-toluenesulfonic acid / methanol / 6 h / 0 °C

4: pyridine / 4-dimethylaminopyridine

With pyridine; toluene-4-sulfonic acid; dmap; In methanol;

DOI:10.1016/0008-6215(90)84126-F

Reference yield:

4-Bromo-benzoic acid (2R,4aR,6S,7S,8S,8aR)-6-methoxy-8-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester → 4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-methoxy-4-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-tetrahydro-pyran-3-yl ester (109889-84-1,116215-19-1,128796-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-toluenesulfonic acid / methanol / 6 h / 0 °C

2: pyridine / 4-dimethylaminopyridine

With pyridine; toluene-4-sulfonic acid; dmap; In methanol;

DOI:10.1016/0008-6215(90)84126-F

Reference yield:

methyl-4,6-O-phenylmethylene-α-D-mannopyranoside (3162-96-7,4148-58-7,4153-17-7,4288-93-1,5328-47-2,6988-39-2,13566-32-0,14155-23-8,27994-50-9,37093-57-5,37093-59-7,57701-27-6,59168-66-0,64552-06-3,65391-13-1,65391-14-2,65530-26-9,66512-65-0,71117-36-7,71117-37-8,71117-41-4,72904-85-9,74560-56-8,79549-74-9,86783-81-5,96093-51-5,98633-13-7,110415-35-5,110415-36-6,110850-29-8,124020-29-7,126924-12-7,129263-21-4,131433-03-9,145920-49-6,146863-04-9) → 4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-methoxy-4-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-tetrahydro-pyran-3-yl ester (109889-84-1,116215-19-1,128796-76-9)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 4-dimethylaminopyridine

2: pyridine / 4-dimethylaminopyridine

3: 4-toluenesulfonic acid / methanol / 6 h / 0 °C

4: pyridine / 4-dimethylaminopyridine

With pyridine; toluene-4-sulfonic acid; dmap; In methanol;

DOI:10.1016/0008-6215(90)84126-F

upstream raw materials:

4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-5-hydroxy-6-hydroxymethyl-2-methoxy-4-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-tetrahydro-pyran-3-yl ester

acetic anhydride

(E)-3-(4-methoxyphenyl)propenoyl chloride

methyl-4,6-O-phenylmethylene-α-D-mannopyranoside

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