(S)-2-((4R,5S)-4,8-Dimethyl-spiro[4.5]deca-1,7-dien-1-yl)-2-hydroxy-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Base Information

• Chemical Name: (S)-2-((4R,5S)-4,8-Dimethyl-spiro[4.5]deca-1,7-dien-1-yl)-2-hydroxy-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
• CAS No.: 306292-47-7
• Molecular Formula: C₃₁H₄₄O₃
• Molecular Weight: 464.689
• Mol file: 306292-47-7.mol

Synonyms:(S)-2-((4R,5S)-4,8-Dimethyl-spiro[4.5]deca-1,7-dien-1-yl)-2-hydroxy-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Chemical Property of (S)-2-((4R,5S)-4,8-Dimethyl-spiro[4.5]deca-1,7-dien-1-yl)-2-hydroxy-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((4R,5S)-4,8-Dimethyl-spiro[4.5]deca-1,7-dien-1-yl)-2-hydroxy-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

There total 4 articles about (S)-2-((4R,5S)-4,8-Dimethyl-spiro[4.5]deca-1,7-dien-1-yl)-2-hydroxy-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl 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: 55.0%

2-Oxopropansaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>ester (88292-41-5) + C27H42N2O2S → (S)-2-((4R,5S)-4,8-Dimethyl-spiro[4.5]deca-1,7-dien-1-yl)-2-hydroxy-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (306292-47-7)

Guidance literature:

C₂₇H₄₂N₂O₂S; With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; at -78 - -20 ℃;

With magnesium bromide diethyl etherate; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 0.166667h;

2-Oxopropansaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>ester; In tetrahydrofuran; diethyl ether; hexane; at -78 - 20 ℃; for 0.166667h; Further stages.;

DOI:10.1021/ja0026758

Reference yield: 55.0%

2-Oxopropansaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>ester (88292-41-5) + C27H42N2O2S (306292-46-6) → (S)-2-((4R,5S)-4,8-Dimethyl-spiro[4.5]deca-1,7-dien-1-yl)-2-hydroxy-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (306292-47-7)

Guidance literature:

C₂₇H₄₂N₂O₂S; With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; at -78 - -20 ℃;

With magnesium bromide; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 0.166667h;

2-Oxopropansaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>ester; In tetrahydrofuran; diethyl ether; hexane; at -78 - 20 ℃;

DOI:10.1016/S0040-4020(03)00936-0

Reference yield:

(-)-8-phenylmenthol (65253-04-5) → (S)-2-((4R,5S)-4,8-Dimethyl-spiro[4.5]deca-1,7-dien-1-yl)-2-hydroxy-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (306292-47-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: p-TsOH / benzene / Heating

2.1: n-BuLi / diethyl ether; tetrahydrofuran; hexane / -78 - -20 °C

2.2: magnesium bromide diethyletherate / tetrahydrofuran; diethyl ether; hexane / 0.17 h / -78 °C

2.3: 55 percent / tetrahydrofuran; diethyl ether; hexane / 0.17 h / -78 - 20 °C

With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; benzene;

DOI:10.1021/ja0026758

upstream raw materials:

2-Oxopropansaeure-<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>ester

C₂₇H₄₂N₂O₂S

(4R,5S)-4,8-Dimethyl-spiro[4.5]dec-7-en-1-one

(-)-8-phenylmenthol

Downstream raw materials:

(S)-2-((4R,5S)-4,8-Dimethyl-spiro[4.5]deca-1,7-dien-1-yl)-2-(2-trimethylsilanyl-ethoxymethoxy)-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester