(3E,5E)-6-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-2-hydroxy-hexa-3,5-dienenitrile

Base Information

Chemical Name:(3E,5E)-6-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-2-hydroxy-hexa-3,5-dienenitrile
CAS No.:339291-78-0
Molecular Formula:C₂₅H₃₂ClNO₃
Molecular Weight:429.987
Hs Code.:

Synonyms:(3E,5E)-6-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-2-hydroxy-hexa-3,5-dienenitrile

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Chemical Property of (3E,5E)-6-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-2-hydroxy-hexa-3,5-dienenitrile

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Technology Process of (3E,5E)-6-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-2-hydroxy-hexa-3,5-dienenitrile

There total 16 articles about (3E,5E)-6-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-2-hydroxy-hexa-3,5-dienenitrile 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:

: (3E,5E)-6-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-2-trimethylsilanyloxy-hexa-3,5-dienenitrile

: 339291-78-0
(3E,5E)-6-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-2-hydroxy-hexa-3,5-dienenitrile

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; water; for 0.5h;
DOI:10.1021/jo005683f

Reference yield:

: 2403-58-9
4-methoxybenzaldehyde diethylacetal

: 339291-78-0
(3E,5E)-6-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-2-hydroxy-hexa-3,5-dienenitrile

Guidance literature:: Multi-step reaction with 14 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

6.1: 73 percent / DMAP / dimethylformamide / 20 °C

7.1: 93 percent / Dess-Martin perioninane / CH₂Cl₂ / 4 h / 20 °C

8.1: 70 percent / LiOH*H₂O; molecular sieves 4 Angstroeme / tetrahydrofuran / 11 h / Heating

9.1: 95 percent / CSA / methanol / 2 h / 20 °C

10.1: 83 percent / LiCl; Et₃N; CH₃SO₂Cl / dimethylformamide / 10 h / 20 °C

11.1: 86 percent / DIBAL / hexane; CH₂Cl₂ / 7 h / 20 °C

12.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

13.1: KCN; 18-crown-6 / CH₂Cl₂ / 3 h / 20 °C

14.1: HCl / tetrahydrofuran; H₂O / 0.5 h

With hydrogenchloride; dmap; potassium cyanide; lithium hydroxide; oxalyl dichloride; 18-crown-6 ether; 4 A molecular sieve; camphor-10-sulfonic acid; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; acetonitrile; lithium chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; water; 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

: 339291-78-0
(3E,5E)-6-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-2-hydroxy-hexa-3,5-dienenitrile

Guidance literature:: Multi-step reaction with 14 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

6.1: 73 percent / DMAP / dimethylformamide / 20 °C

7.1: 93 percent / Dess-Martin perioninane / CH₂Cl₂ / 4 h / 20 °C

8.1: 70 percent / LiOH*H₂O; molecular sieves 4 Angstroeme / tetrahydrofuran / 11 h / Heating

9.1: 95 percent / CSA / methanol / 2 h / 20 °C

10.1: 83 percent / LiCl; Et₃N; CH₃SO₂Cl / dimethylformamide / 10 h / 20 °C

11.1: 86 percent / DIBAL / hexane; CH₂Cl₂ / 7 h / 20 °C

12.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

13.1: KCN; 18-crown-6 / CH₂Cl₂ / 3 h / 20 °C

14.1: HCl / tetrahydrofuran; H₂O / 0.5 h

With hydrogenchloride; dmap; potassium cyanide; lithium hydroxide; oxalyl dichloride; 18-crown-6 ether; 4 A molecular sieve; camphor-10-sulfonic acid; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; acetonitrile; lithium chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; 3.1: Swern oxidation;
DOI:10.1021/jo005683f