(Z)-4-[(1S,2R,3R)-2-Hydroxymethyl-3-(4-methoxy-benzyloxy)-1-methyl-cyclopentyl]-2-methyl-but-2-en-1-ol

Base Information

Chemical Name:(Z)-4-[(1S,2R,3R)-2-Hydroxymethyl-3-(4-methoxy-benzyloxy)-1-methyl-cyclopentyl]-2-methyl-but-2-en-1-ol
CAS No.:339291-64-4
Molecular Formula:C₂₀H₃₀O₄
Molecular Weight:334.456
Hs Code.:

Synonyms:(Z)-4-[(1S,2R,3R)-2-Hydroxymethyl-3-(4-methoxy-benzyloxy)-1-methyl-cyclopentyl]-2-methyl-but-2-en-1-ol

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Chemical Property of (Z)-4-[(1S,2R,3R)-2-Hydroxymethyl-3-(4-methoxy-benzyloxy)-1-methyl-cyclopentyl]-2-methyl-but-2-en-1-ol

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Technology Process of (Z)-4-[(1S,2R,3R)-2-Hydroxymethyl-3-(4-methoxy-benzyloxy)-1-methyl-cyclopentyl]-2-methyl-but-2-en-1-ol

There total 7 articles about (Z)-4-[(1S,2R,3R)-2-Hydroxymethyl-3-(4-methoxy-benzyloxy)-1-methyl-cyclopentyl]-2-methyl-but-2-en-1-ol 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: 97.0%

: 339291-63-3
(Z)-4-[(2S,4aR,5S,7aR)-2-(4-Methoxy-phenyl)-5-methyl-hexahydro-cyclopenta[1,3]dioxin-5-yl]-2-methyl-but-2-enoic acid ethyl ester

: 339291-64-4
(Z)-4-[(1S,2R,3R)-2-Hydroxymethyl-3-(4-methoxy-benzyloxy)-1-methyl-cyclopentyl]-2-methyl-but-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 - 20 ℃;
DOI:10.1021/jo005683f

Reference yield:

: 2403-58-9
4-methoxybenzaldehyde diethylacetal

: 339291-64-4
(Z)-4-[(1S,2R,3R)-2-Hydroxymethyl-3-(4-methoxy-benzyloxy)-1-methyl-cyclopentyl]-2-methyl-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 26.5 g / dimethylformamide / 3 h / 50 °C / 10 - 15 Torr

2.1: 83 percent / DIBAL / CH₂Cl₂; cyclohexane / 5 h / -78 °C

3.1: DMSO; oxalyl chloride; Et₃N

4.1: 18-crown-6/acetonitrile complex; KHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 1.788 g / tetrahydrofuran / 1 h / -78 °C

5.1: 97 percent / DIBAL / hexane; CH₂Cl₂ / -78 - 20 °C

With oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; acetonitrile; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; 3.1: Swern oxidation;
DOI:10.1021/jo005683f

Reference yield:

: ((2R,3R)-3-Hydroxy-2-hydroxymethyl-1-methyl-cyclopentyl)-acetic acid methyl ester

: 339291-64-4
(Z)-4-[(1S,2R,3R)-2-Hydroxymethyl-3-(4-methoxy-benzyloxy)-1-methyl-cyclopentyl]-2-methyl-but-2-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 26.5 g / dimethylformamide / 3 h / 50 °C / 10 - 15 Torr

2.1: 83 percent / DIBAL / CH₂Cl₂; cyclohexane / 5 h / -78 °C

3.1: DMSO; oxalyl chloride; Et₃N

4.1: 18-crown-6/acetonitrile complex; KHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 1.788 g / tetrahydrofuran / 1 h / -78 °C

5.1: 97 percent / DIBAL / hexane; CH₂Cl₂ / -78 - 20 °C

With oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; acetonitrile; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; 3.1: Swern oxidation;
DOI:10.1021/jo005683f