(S)-2-decanyl tosylate

Base Information

• Chemical Name: (S)-2-decanyl tosylate
• CAS No.: 163847-46-9
• Molecular Formula: C₁₇H₂₈O₃S
• Molecular Weight: 312.474
• Mol file: 163847-46-9.mol

Synonyms:(S)-2-decanyl tosylate

Chemical Property of (S)-2-decanyl tosylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-decanyl tosylate

There total 1 articles about (S)-2-decanyl tosylate 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: 93.0%

(S)-decan-2-ol (33758-16-6) + p-toluenesulfonyl chloride (98-59-9) → (S)-2-decanyl tosylate (163847-46-9)

Guidance literature:

With trimethylamine hydrochloride; triethylamine; In dichloromethane; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.05.023

Reference yield: 72.0%

(S)-2-decanyl tosylate (163847-46-9) + Methyl p-tolyl sulfone (3185-99-7) → (R)-2-methyl-1-(4-methylphenylsulfonyl)decane (1393538-45-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 55 ℃; optical yield given as %ee; stereospecific reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.05.023

Reference yield:

(S)-2-decanyl tosylate (163847-46-9) → (5S,9R)-5,9-dimethyl-8-(4-methylphenylsulfonyl)heptadecane (1393538-53-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0 - 55 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - -35 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1016/j.tetasy.2012.05.023

upstream raw materials:

(S)-decan-2-ol

p-toluenesulfonyl chloride

Downstream raw materials:

(5S,9R)-5,9-dimethyl-8-(4-methylphenylsulfonyl)heptadecane

(5R,9R)-5,9-dimethyl-8-(4-methylphenylsulfonyl)heptadecane

(R)-2-methyl-1-(4-methylphenylsulfonyl)decane

Refernces