(1R,2S,4R,5R,8S)-8-Ethoxycarbonylmethyl-2-(2-ethoxycarbonylmethyl-4,5-dimethoxy-phenyl)-4-hydroxy-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-1-carboxylic acid

Base Information

Chemical Name:(1R,2S,4R,5R,8S)-8-Ethoxycarbonylmethyl-2-(2-ethoxycarbonylmethyl-4,5-dimethoxy-phenyl)-4-hydroxy-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-1-carboxylic acid
CAS No.:103225-60-1
Molecular Formula:C₂₅H₃₂O₁₁
Molecular Weight:508.522
Hs Code.:

(1R,2S,4R,5R,8S)-8-Ethoxycarbonylmethyl-2-(2-ethoxycarbonylmethyl-4,5-dimethoxy-phenyl)-4-hydroxy-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-1-carboxylic acid

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Chemical Property of (1R,2S,4R,5R,8S)-8-Ethoxycarbonylmethyl-2-(2-ethoxycarbonylmethyl-4,5-dimethoxy-phenyl)-4-hydroxy-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-1-carboxylic acid

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Technology Process of (1R,2S,4R,5R,8S)-8-Ethoxycarbonylmethyl-2-(2-ethoxycarbonylmethyl-4,5-dimethoxy-phenyl)-4-hydroxy-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-1-carboxylic acid

There total 4 articles about (1R,2S,4R,5R,8S)-8-Ethoxycarbonylmethyl-2-(2-ethoxycarbonylmethyl-4,5-dimethoxy-phenyl)-4-hydroxy-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-1-carboxylic acid 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:

: 73053-80-2
ethyl 2-(bromomethyl)-4,5-dimethoxyphenylacetate

: 103225-60-1
(1R,2S,4R,5R,8S)-8-Ethoxycarbonylmethyl-2-(2-ethoxycarbonylmethyl-4,5-dimethoxy-phenyl)-4-hydroxy-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-1-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / (Bu₄N)2Cr₂O₇ / CHCl₃ / 2 h / Heating

2: 92 percent / piperidine, glacial acetic acid / benzene / 3 h / Heating

3: toluene / 72 h / Heating

4: 1.) MCPBA, 2.) 3N aq. HClO₄ / 1.) CH₂Cl₂, from o deg C to RT, 2 h, 2.) THF, RT, 12 h

With piperidine; perchloric acid; (Bu₄N)2Cr₂O₇; acetic acid; 3-chloro-benzenecarboperoxoic acid; In chloroform; toluene; benzene;
DOI:10.1021/jo00367a017

Reference yield:

: 103225-55-4
ethyl 2-(2-formyl-4,5-dimethoxyphenyl)acetate

: 103225-60-1
(1R,2S,4R,5R,8S)-8-Ethoxycarbonylmethyl-2-(2-ethoxycarbonylmethyl-4,5-dimethoxy-phenyl)-4-hydroxy-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-1-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / piperidine, glacial acetic acid / benzene / 3 h / Heating

2: toluene / 72 h / Heating

3: 1.) MCPBA, 2.) 3N aq. HClO₄ / 1.) CH₂Cl₂, from o deg C to RT, 2 h, 2.) THF, RT, 12 h

With piperidine; perchloric acid; acetic acid; 3-chloro-benzenecarboperoxoic acid; In toluene; benzene;
DOI:10.1021/jo00367a017

Reference yield:

: 103225-56-5
[2-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-4,5-dimethoxy-phenyl]-acetic acid ethyl ester

: 103225-60-1
(1R,2S,4R,5R,8S)-8-Ethoxycarbonylmethyl-2-(2-ethoxycarbonylmethyl-4,5-dimethoxy-phenyl)-4-hydroxy-5-methyl-7-oxo-6-oxa-bicyclo[3.2.1]octane-1-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: toluene / 72 h / Heating

2: 1.) MCPBA, 2.) 3N aq. HClO₄ / 1.) CH₂Cl₂, from o deg C to RT, 2 h, 2.) THF, RT, 12 h

With perchloric acid; 3-chloro-benzenecarboperoxoic acid; In toluene;
DOI:10.1021/jo00367a017