(Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid (2R,4aS,7S,8S,8aS)-7-benzyloxy-3-formyl-4a,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester

Base Information

• Chemical Name: (Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid (2R,4aS,7S,8S,8aS)-7-benzyloxy-3-formyl-4a,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester
• CAS No.: 84132-50-3
• Molecular Formula: C₃₂H₃₆O₄S
• Molecular Weight: 516.701
• Mol file: 84132-50-3.mol

Synonyms:(Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid (2R,4aS,7S,8S,8aS)-7-benzyloxy-3-formyl-4a,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester

Chemical Property of (Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid (2R,4aS,7S,8S,8aS)-7-benzyloxy-3-formyl-4a,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid (2R,4aS,7S,8S,8aS)-7-benzyloxy-3-formyl-4a,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester

There total 16 articles about (Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid (2R,4aS,7S,8S,8aS)-7-benzyloxy-3-formyl-4a,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl 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: 72.0%

(Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid (2R,4aS,7S,8S,8aS)-7-benzyloxy-3-[1,3]dioxolan-2-yl-4a,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester (84143-11-3) → (Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid (2R,4aS,7S,8S,8aS)-7-benzyloxy-3-formyl-4a,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester (84132-50-3)

Guidance literature:

With hydrogenchloride; acetic acid; In tetrahydrofuran;

DOI:10.1021/jo00152a012

Reference yield:

3',4',4'a,5',6',7'-hexahydro-4'a,8-dimethylspiro<1,3-dioxolane-2,2'(1'H)-naphthalene> (65898-63-7) → (Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid (2R,4aS,7S,8S,8aS)-7-benzyloxy-3-formyl-4a,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester (84132-50-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 63 percent / chromium trioxide - dipyridine complex / CH₂Cl₂

2: 69 percent / liq. NH₃, Li / ethanol; tetrahydrofuran

3: 71 percent / NaH / tetrahydrofuran

4: 89 percent / aq. HCl, AcOH / tetrahydrofuran

5: 93 percent / sodium methoxide

6: 64 percent / DDQ

7: 85 percent / p-TsOH / 3.5 h / 25 °C

8: 55 percent / L-Selectride / tetrahydrofuran / 2 h / 0 °C

9: 53 percent / DCC / tetrahydrofuran / 1.) 24 h, 0 deg C, 2.) 24 h, 25 deg C

10: 72 percent / aq. HCl, AcOH / tetrahydrofuran

With hydrogenchloride; 2,2'-bipyridine-chromium(VI) oxide; ammonia; sodium methylate; lithium; L-Selectride; sodium hydride; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jo00152a012

Reference yield:

3',4',4'a,5',6',7',8',8'aα-octahydro-4'aβ,8'α-dimethylspiro-<1,3-dioxolane-2,2'(1'H)-naphthalen-7'β-ol> (84132-42-3) → (Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid (2R,4aS,7S,8S,8aS)-7-benzyloxy-3-formyl-4a,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester (84132-50-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 71 percent / NaH / tetrahydrofuran

2: 89 percent / aq. HCl, AcOH / tetrahydrofuran

3: 93 percent / sodium methoxide

4: 64 percent / DDQ

5: 85 percent / p-TsOH / 3.5 h / 25 °C

6: 55 percent / L-Selectride / tetrahydrofuran / 2 h / 0 °C

7: 53 percent / DCC / tetrahydrofuran / 1.) 24 h, 0 deg C, 2.) 24 h, 25 deg C

8: 72 percent / aq. HCl, AcOH / tetrahydrofuran

With hydrogenchloride; sodium methylate; L-Selectride; sodium hydride; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran;

DOI:10.1021/jo00152a012

upstream raw materials:

(Z)-4-Phenylsulfanyl-hexa-3,5-dienoic acid (2R,4aS,7S,8S,8aS)-7-benzyloxy-3-[1,3]dioxolan-2-yl-4a,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl ester

3',4',4'a,5',6',7'-hexahydro-4'a,8-dimethylspiro<1,3-dioxolane-2,2'(1'H)-naphthalene>

3',4',4'a,5',6',7',8',8'aα-octahydro-4'aβ,8'α-dimethylspiro-<1,3-dioxolane-2,2'(1'H)-naphthalen-7'β-ol>

ethyl 4-(phenylthio)-2,4-hexadienoate