(4RS,5S,8R)-3,8-dimethyl-5-[(1S)-1,5-dimethyl-3-phenylsulfonylhex-4-enyl]-1-methoxy-5,6,7,8-tetrahydronaphthalene

Base Information

• Chemical Name: (4RS,5S,8R)-3,8-dimethyl-5-[(1S)-1,5-dimethyl-3-phenylsulfonylhex-4-enyl]-1-methoxy-5,6,7,8-tetrahydronaphthalene
• CAS No.: 404366-99-0
• Molecular Formula: C₂₇H₃₆O₃S
• Molecular Weight: 440.647
• Mol file: 404366-99-0.mol

Synonyms:(4RS,5S,8R)-3,8-dimethyl-5-[(1S)-1,5-dimethyl-3-phenylsulfonylhex-4-enyl]-1-methoxy-5,6,7,8-tetrahydronaphthalene

Chemical Property of (4RS,5S,8R)-3,8-dimethyl-5-[(1S)-1,5-dimethyl-3-phenylsulfonylhex-4-enyl]-1-methoxy-5,6,7,8-tetrahydronaphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4RS,5S,8R)-3,8-dimethyl-5-[(1S)-1,5-dimethyl-3-phenylsulfonylhex-4-enyl]-1-methoxy-5,6,7,8-tetrahydronaphthalene

There total 11 articles about (4RS,5S,8R)-3,8-dimethyl-5-[(1S)-1,5-dimethyl-3-phenylsulfonylhex-4-enyl]-1-methoxy-5,6,7,8-tetrahydronaphthalene 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: 91.0%

C6H5SO2CH(Li)CHC(CH3)2 (181698-29-3) + (5R,8R)-3,8-dimethyl-1-methoxy-5-[(S)-1-methyl-2-(p-tolylsulfonyl)oxyethyl]-5,6,7,8-tetrahydronaphthalene (181698-25-9) → (4RS,5S,8R)-3,8-dimethyl-5-[(1S)-1,5-dimethyl-3-phenylsulfonylhex-4-enyl]-1-methoxy-5,6,7,8-tetrahydronaphthalene (404366-99-0)

Guidance literature:

In tetrahydrofuran;

DOI:10.1039/cc9960001743

Reference yield: 76.0%

3-methyl-1-(phenylsulfonyl)but-2-ene (15874-80-3) + (5R,8R)-3,8-dimethyl-1-methoxy-5-[(S)-1-methyl-2-(p-tolylsulfonyl)oxyethyl]-5,6,7,8-tetrahydronaphthalene (181698-25-9) → (4RS,5S,8R)-3,8-dimethyl-5-[(1S)-1,5-dimethyl-3-phenylsulfonylhex-4-enyl]-1-methoxy-5,6,7,8-tetrahydronaphthalene (404366-99-0)

Guidance literature:

3-methyl-1-(phenylsulfonyl)but-2-ene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -30 ℃; for 2h;

(5R,8R)-3,8-dimethyl-1-methoxy-5-[(S)-1-methyl-2-(p-tolylsulfonyl)oxyethyl]-5,6,7,8-tetrahydronaphthalene; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 4h;

DOI:10.1039/b102961b

Reference yield:

(+)-neoisopulegol (20549-46-6) → (4RS,5S,8R)-3,8-dimethyl-5-[(1S)-1,5-dimethyl-3-phenylsulfonylhex-4-enyl]-1-methoxy-5,6,7,8-tetrahydronaphthalene (404366-99-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 88 percent / t-BuOOH / VO(acac)2 / benzene / 20 °C

2.1: 79 percent / NaBH₃CN; BF₃*OEt₂; bromocresol green / tetrahydrofuran / 12 h / 20 °C

3.1: 84 percent / imidazole / dimethylformamide / 0.25 h / 20 °C

4.1: 88 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3.5 h / -65 - 20 °C

5.1: LHMDS / tetrahydrofuran / 0.83 h / -85 °C

5.2: HMPA / tetrahydrofuran / 1.92 h / -85 - 0 °C

6.1: LHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 2.35 g / tetrahydrofuran; hexane / 13 h / -78 - 20 °C

7.1: Mg / tetrahydrofuran

7.2: tetrahydrofuran / 1.5 h / 20 °C

8.1: 1.61 g / BF₃*OEt₂ / tetrahydrofuran / 18 h / -40 - 20 °C

9.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 20 °C

10.1: BuLi / tetrahydrofuran; hexane / 2 h / -78 - -30 °C

10.2: 76 percent / tetrahydrofuran; hexane / 4 h / -78 - 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; dmap; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; bromocresol green; sodium cyanoborohydride; magnesium; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 4.1: Swern oxidation;

DOI:10.1039/b102961b

upstream raw materials:

C₆H₅SO₂CH(Li)CHC(CH₃)2

(5R,8R)-3,8-dimethyl-1-methoxy-5-[(S)-1-methyl-2-(p-tolylsulfonyl)oxyethyl]-5,6,7,8-tetrahydronaphthalene

3-methyl-1-(phenylsulfonyl)but-2-ene

(+)-neoisopulegol