(1R,2R,αR,Rs)-(+)-(5,5-dimethyl-2-isopropenyl)-α-p-toluenesulfinylhexaneacetate

Base Information

• Chemical Name: (1R,2R,αR,Rs)-(+)-(5,5-dimethyl-2-isopropenyl)-α-p-toluenesulfinylhexaneacetate
• CAS No.: 151324-12-8
• Molecular Formula: C₂₁H₃₀O₃S
• Molecular Weight: 362.533
• Mol file: 151324-12-8.mol

Synonyms:

Chemical Property of (1R,2R,αR,Rs)-(+)-(5,5-dimethyl-2-isopropenyl)-α-p-toluenesulfinylhexaneacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,αR,Rs)-(+)-(5,5-dimethyl-2-isopropenyl)-α-p-toluenesulfinylhexaneacetate

There total 4 articles about (1R,2R,αR,Rs)-(+)-(5,5-dimethyl-2-isopropenyl)-α-p-toluenesulfinylhexaneacetate 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:

methyl (S)-(+)-2-p-toluenesulfinyl-5,5,9-trimethyl-2,8-decadienoate → (1R,2R,αR,Rs)-(+)-(5,5-dimethyl-2-isopropenyl)-α-p-toluenesulfinylhexaneacetate (151324-12-8) + (1S,2S,αS,Rs)-(+)-(5,5-dimethyl-2-isopropenyl)-α-p-toluenesulfinylhexaneacetate

Guidance literature:

With diethylaluminium chloride; In dichloromethane; at -78 ℃; for 12h; Yield given. Yields of byproduct given;

DOI:10.1248/cpb.41.666

Reference yield:

tert-butyl (R)-p-toluenesulfinylacetate (58059-08-8) → (1R,2R,αR,Rs)-(+)-(5,5-dimethyl-2-isopropenyl)-α-p-toluenesulfinylhexaneacetate (151324-12-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / sodium methoxide / 4 h / Ambient temperature

2: 86 percent / piperidinium acetate, molecular sieves 4A / benzene / 72 h / Ambient temperature

3: EtAlCl₂ / CH₂Cl₂ / 12 h / -78 °C

With 4 A molecular sieve; sodium methylate; ethylaluminum dichloride; piperdinium acetate; In dichloromethane; benzene;

DOI:10.1248/cpb.41.666

Reference yield:

(R)-(+)-methyl-α-(para-tolylsulfinyl) acetate (102340-68-1) → (1R,2R,αR,Rs)-(+)-(5,5-dimethyl-2-isopropenyl)-α-p-toluenesulfinylhexaneacetate (151324-12-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / piperidinium acetate, molecular sieves 4A / benzene / 72 h / Ambient temperature

2: EtAlCl₂ / CH₂Cl₂ / 12 h / -78 °C

With 4 A molecular sieve; ethylaluminum dichloride; piperdinium acetate; In dichloromethane; benzene;

DOI:10.1248/cpb.41.666

upstream raw materials:

tert-butyl (R)-p-toluenesulfinylacetate

(R)-(+)-methyl-α-(para-tolylsulfinyl) acetate

(-)-(S_S)-(toluene-4-sulfinyl)-acetic acid tert-butyl ester

Downstream raw materials:

methyl (S)-(-)-1(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)acetate

(S)-(-)-1(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)etanol

(S)-(-)-1-(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)-2-propanone

(S)-(-)-1(E)-(5,5-dimethyl-2-isopropenylcyclohexylidene)acetaldehyde

Refernces