dimethyl 6-exo-acetoxy-2,3-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene-5,5-dicarboxylate

Base Information

• Chemical Name: dimethyl 6-exo-acetoxy-2,3-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene-5,5-dicarboxylate
• CAS No.: 115479-55-5
• Molecular Formula: C₂₆H₂₆O₉
• Molecular Weight: 482.487
• Mol file: 115479-55-5.mol

Synonyms:dimethyl 6-exo-acetoxy-2,3-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene-5,5-dicarboxylate

Chemical Property of dimethyl 6-exo-acetoxy-2,3-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene-5,5-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl 6-exo-acetoxy-2,3-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene-5,5-dicarboxylate

There total 3 articles about dimethyl 6-exo-acetoxy-2,3-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene-5,5-dicarboxylate 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: 57.0%

3,4-bis(benzoloxy)furan (53996-40-0) + dimethyl (acetoxymethylene)malonate (88456-30-8) → dimethyl 6-exo-acetoxy-2,3-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene-5,5-dicarboxylate (115479-55-5)

Guidance literature:

In benzene; at 40 ℃; for 96h;

DOI:10.1021/jo00258a013

Reference yield:

hydroxymethylenemalonic acid dimethyl ester (27931-91-5) → dimethyl 6-exo-acetoxy-2,3-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene-5,5-dicarboxylate (115479-55-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / pyridine / 3 h / Ambient temperature

2: 57 percent / benzene / 96 h / 40 °C

With pyridine; In benzene;

DOI:10.1021/jo00258a013

Reference yield:

dimethyl (methoxymethylene)malonate (22398-14-7) → dimethyl 6-exo-acetoxy-2,3-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene-5,5-dicarboxylate (115479-55-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / 1.5percent aq. NaOH / 0.5 h / 0 °C

2: 78 percent / pyridine / 3 h / Ambient temperature

3: 57 percent / benzene / 96 h / 40 °C

With pyridine; sodium hydroxide; In benzene;

DOI:10.1021/jo00258a013

upstream raw materials:

3,4-bis(benzoloxy)furan

dimethyl (acetoxymethylene)malonate

hydroxymethylenemalonic acid dimethyl ester

dimethyl (methoxymethylene)malonate

Downstream raw materials:

3-Acetoxy-2-((2S,3S,4R,5S)-5-acetoxy-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-propionic acid methyl ester

2-((2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yl)-3-hydroxy-propionic acid methyl ester

dimethyl <5β-acetoxy-3α,4α-bis(benzyloxy)tetrahydro-2H-pyran-2β-yl>malonate

dimethyl <3α,4α-bis(benzyloxy)-5β-hydroxytetrahydro-2H-pyran-2β-yl>malonate