(S)-2-hydroxy-4-methylpent-4-en-1-yl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (S)-2-hydroxy-4-methylpent-4-en-1-yl 4-methylbenzenesulfonate
• CAS No.: 1376854-43-1
• Molecular Formula: C₁₃H₁₈O₄S
• Molecular Weight: 270.35
• Mol file: 1376854-43-1.mol

Synonyms:(S)-2-hydroxy-4-methylpent-4-en-1-yl 4-methylbenzenesulfonate

Chemical Property of (S)-2-hydroxy-4-methylpent-4-en-1-yl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-hydroxy-4-methylpent-4-en-1-yl 4-methylbenzenesulfonate

There total 2 articles about (S)-2-hydroxy-4-methylpent-4-en-1-yl 4-methylbenzenesulfonate 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: 90.0%

isopropenylmagnesium bromide (13291-18-4) + (S)-Glycidyl tosylate (70987-78-9,6746-81-2) → (S)-2-hydroxy-4-methylpent-4-en-1-yl 4-methylbenzenesulfonate (1376854-43-1)

Guidance literature:

isopropenylmagnesium bromide; With copper(l) iodide; In tetrahydrofuran; at -78 ℃; for 0.75h; Inert atmosphere;

(S)-Glycidyl tosylate; In tetrahydrofuran; at -78 - -40 ℃; for 2.5h; Inert atmosphere;

DOI:10.1021/ol301068h

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (S)-2-hydroxy-4-methylpent-4-en-1-yl 4-methylbenzenesulfonate (1376854-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; triethylamine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

2.1: copper(l) iodide / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

2.2: 2.5 h / -78 - -40 °C / Inert atmosphere

With dmap; copper(l) iodide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol301068h

Reference yield: 85.0%

2-(phenylselanyl)acetic acid (17893-46-8) + (S)-2-hydroxy-4-methylpent-4-en-1-yl 4-methylbenzenesulfonate (1376854-43-1) → (5S)-5-(2-methylallyl)-3-(phenylselanyl)dihydrofuran-2(3H)-one (1376854-00-0)

Guidance literature:

2-(phenylselanyl)acetic acid; With n-butyllithium; diisopropylamine; In tetrahydrofuran; at -10 - 20 ℃; for 2.33333h; Inert atmosphere;

(S)-2-hydroxy-4-methylpent-4-en-1-yl 4-methylbenzenesulfonate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 1h; Inert atmosphere;

With dmap; diisopropyl-carbodiimide; In dichloromethane; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/anie.201400617

upstream raw materials:

isopropenylmagnesium bromide

(S)-Glycidyl tosylate

p-toluenesulfonyl chloride

Downstream raw materials:

(5S)-5-(2-methylallyl)-3-(phenylselanyl)dihydrofuran-2(3H)-one

methyl-2-((1S,2R,3S)-2-(2-hydroxy-2-((5S)-5-(2-methylallyl)-2-oxo-3-(phenylselanyl)tetrahydrofuran-3-yl)ethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate