(1R, 2S, 3R, 4R)-4-benzoyloxy-2-(dimethoxymethyl)-3-methyl-1-cyclopentaneacetic acid methyl ester

Base Information

Chemical Name:(1R, 2S, 3R, 4R)-4-benzoyloxy-2-(dimethoxymethyl)-3-methyl-1-cyclopentaneacetic acid methyl ester
CAS No.:108377-15-7
Molecular Formula:C₁₉H₂₆O₆
Molecular Weight:350.412
Hs Code.:

Synonyms:(1R, 2S, 3R, 4R)-4-benzoyloxy-2-(dimethoxymethyl)-3-methyl-1-cyclopentaneacetic acid methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R, 2S, 3R, 4R)-4-benzoyloxy-2-(dimethoxymethyl)-3-methyl-1-cyclopentaneacetic acid methyl ester

Chemical Property:

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Technology Process of (1R, 2S, 3R, 4R)-4-benzoyloxy-2-(dimethoxymethyl)-3-methyl-1-cyclopentaneacetic acid methyl ester

There total 8 articles about (1R, 2S, 3R, 4R)-4-benzoyloxy-2-(dimethoxymethyl)-3-methyl-1-cyclopentaneacetic acid methyl 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: 76.0%

: 108377-14-6
(1R, 2S, 3R, 4R)-2-(dimethoxymethyl)-4-hydroxyl-3-methyl-1-cyclopentane acetic acid methyl ester

: 65-85-0,8013-63-6
benzoic acid

: 108377-15-7
(1R, 2S, 3R, 4R)-4-benzoyloxy-2-(dimethoxymethyl)-3-methyl-1-cyclopentaneacetic acid methyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 16h; Ambient temperature;
DOI:10.1016/S0040-4020(01)87559-1

Reference yield:

: 108448-78-8
(1R, 2R, 4R, 5R)-4-exo-methyl-tricyclo<(3.2.1.1)^3,8>-7-oxa-2-exo-nonanol

: 108377-15-7
(1R, 2S, 3R, 4R)-4-benzoyloxy-2-(dimethoxymethyl)-3-methyl-1-cyclopentaneacetic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / 1.) (COCl)2, DMSO, 2.) Et₃N / CH₂Cl₂ / 1.) -60 deg C, 2.) from -60 deg C to room temperature, 1 h

2: 93 percent / Al-Hg / ethanol; tetrahydrofuran / 1.) 0 deg C, 1 h, 2.) room temperature, 2 h

3: 94 percent / 1.) (COCl)2, DMSO, 2.) Et₃N / CH₂Cl₂ / 1.) -60 deg C, 2.) from -60 deg C to room temperature, 1 h

4: 86 percent / 1.) Me₃SiOTf, 2.) pyridine / CH₂Cl₂ / 3 h / -78 °C

5: 81 percent / mCPBA / CH₂Cl₂ / 16 h / Ambient temperature

6: 95 percent / NaOMe / 16 h / Ambient temperature

7: 76 percent / Ph₃P, diethyldiazodicarboxylate / tetrahydrofuran / 16 h / Ambient temperature

With pyridine; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; aluminium amalgam; sodium methylate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/S0040-4020(01)87559-1

Reference yield:

: 108449-68-9
(5R, 6S)-5-endo-hydroxymethyl-6-exo-methylbicyclo<2.2.1>-2-heptanone

: 108377-15-7
(1R, 2S, 3R, 4R)-4-benzoyloxy-2-(dimethoxymethyl)-3-methyl-1-cyclopentaneacetic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / 1.) (COCl)2, DMSO, 2.) Et₃N / CH₂Cl₂ / 1.) -60 deg C, 2.) from -60 deg C to room temperature, 1 h

2: 86 percent / 1.) Me₃SiOTf, 2.) pyridine / CH₂Cl₂ / 3 h / -78 °C

3: 81 percent / mCPBA / CH₂Cl₂ / 16 h / Ambient temperature

4: 95 percent / NaOMe / 16 h / Ambient temperature

5: 76 percent / Ph₃P, diethyldiazodicarboxylate / tetrahydrofuran / 16 h / Ambient temperature

With pyridine; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sodium methylate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(01)87559-1