(1R)-3-methyl-2-cyclohexenyl (3S)-4-benzyloxy-3-methylbutanoate

Base Information

• Chemical Name: (1R)-3-methyl-2-cyclohexenyl (3S)-4-benzyloxy-3-methylbutanoate
• CAS No.: 181116-43-8
• Molecular Formula: C₁₉H₂₆O₃
• Molecular Weight: 302.414
• Mol file: 181116-43-8.mol

Synonyms:(1R)-3-methyl-2-cyclohexenyl (3S)-4-benzyloxy-3-methylbutanoate

Chemical Property of (1R)-3-methyl-2-cyclohexenyl (3S)-4-benzyloxy-3-methylbutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-3-methyl-2-cyclohexenyl (3S)-4-benzyloxy-3-methylbutanoate

There total 1 articles about (1R)-3-methyl-2-cyclohexenyl (3S)-4-benzyloxy-3-methylbutanoate 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: 98.0%

(R)-3-methylcyclohex-2-en-1-ol (18890-22-7,54423-21-1) + (S)-4-(Benzyloxy)-3-methylbutanoic acid (64190-49-4) → (1R)-3-methyl-2-cyclohexenyl (3S)-4-benzyloxy-3-methylbutanoate (181116-43-8)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/jm980736v

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) + (1R)-3-methyl-2-cyclohexenyl (3S)-4-benzyloxy-3-methylbutanoate (181116-43-8) → [(Z)-(S)-4-Benzyloxy-3-methyl-1-((R)-3-methyl-cyclohex-2-enyloxy)-but-1-enyloxy]-tert-butyl-dimethyl-silane

Guidance literature:

(1R)-3-methyl-2-cyclohexenyl (3S)-4-benzyloxy-3-methylbutanoate; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 - -50 ℃; for 0.5h;

tert-butyldimethylsilyl chloride; In tetrahydrofuran; hexane; for 0.333333h;

DOI:10.1021/jm980736v

Reference yield:

(1R)-3-methyl-2-cyclohexenyl (3S)-4-benzyloxy-3-methylbutanoate (181116-43-8) → (2R,3S)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid (181116-44-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: i-Pr₂NH; n-BuLi; HMPA / hexane; tetrahydrofuran / 0.5 h / -78 - -50 °C

1.2: hexane; tetrahydrofuran / 0.33 h

2.1: hexane; tetrahydrofuran / 16 h / Heating

3.1: 5 percent aq. HCl / 1 h / 20 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; 1.1: Metallation / 1.2: silylation / 2.1: Rearrangement / 3.1: Hydrolysis;

DOI:10.1021/jm980736v

upstream raw materials:

(R)-3-methylcyclohex-2-en-1-ol

(S)-4-(Benzyloxy)-3-methylbutanoic acid

Downstream raw materials:

(2R,3S)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid

(2S,3S)-4-benzyloxy-3-methyl-2-((1S)-1-methyl-2-cyclohexenyl)butanoic acid