(1S,2S,4S)-2-(4-chlorophenylsulfinyl)-1-methyl-7-oxabicyclo[2.2.1]hept-5-ene

Base Information

Chemical Name:(1S,2S,4S)-2-(4-chlorophenylsulfinyl)-1-methyl-7-oxabicyclo[2.2.1]hept-5-ene
CAS No.:1262638-62-9
Molecular Formula:C₁₃H₁₃ClO₂S
Molecular Weight:268.764
Hs Code.:

Synonyms:(1S,2S,4S)-2-(4-chlorophenylsulfinyl)-1-methyl-7-oxabicyclo[2.2.1]hept-5-ene

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Chemical Property of (1S,2S,4S)-2-(4-chlorophenylsulfinyl)-1-methyl-7-oxabicyclo[2.2.1]hept-5-ene

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Technology Process of (1S,2S,4S)-2-(4-chlorophenylsulfinyl)-1-methyl-7-oxabicyclo[2.2.1]hept-5-ene

There total 4 articles about (1S,2S,4S)-2-(4-chlorophenylsulfinyl)-1-methyl-7-oxabicyclo[2.2.1]hept-5-ene 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: 89.0%

: 534-22-5
2-methylfuran

: 217434-85-0
(+)-1-chloro-4-(vinylsulfinyl)benzene

: 1262638-62-9
(1S,2S,4S)-2-(4-chlorophenylsulfinyl)-1-methyl-7-oxabicyclo[2.2.1]hept-5-ene

Guidance literature:: (+)-1-chloro-4-(vinylsulfinyl)benzene; With 2,6-di-tert-butyl-pyridine; t-butyldimethylsiyl triflate; In acetonitrile; at -30 ℃; Inert atmosphere;

2-methylfuran; In acetonitrile; at -30 ℃; for 24h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol102798f

Reference yield:

: 16411-16-8
p-chlorophenyl vinyl sulfide

: 1262638-62-9
(1S,2S,4S)-2-(4-chlorophenylsulfinyl)-1-methyl-7-oxabicyclo[2.2.1]hept-5-ene

Guidance literature:: Multi-step reaction with 4 steps

1.1: dihydrogen peroxide; acetic acid / water / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C / Inert atmosphere

2.2: 4 h / Inert atmosphere; Resolution of racemate

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.01 h / -78 °C / Inert atmosphere

4.1: 2,6-di-tert-butyl-pyridine; t-butyldimethylsiyl triflate / acetonitrile / -30 °C / Inert atmosphere

4.2: 24 h / -30 °C / Inert atmosphere

With 2,6-di-tert-butyl-pyridine; t-butyldimethylsiyl triflate; dihydrogen peroxide; sodium hydride; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; water; acetonitrile; mineral oil; 4.2: Diels-Alder reaction;
DOI:10.1021/ol102798f

Reference yield:

: 1262638-55-0
1-chloro-4-(2-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy)ethylsulfinyl)benzene

: 1262638-62-9
(1S,2S,4S)-2-(4-chlorophenylsulfinyl)-1-methyl-7-oxabicyclo[2.2.1]hept-5-ene

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.01 h / -78 °C / Inert atmosphere

2.1: 2,6-di-tert-butyl-pyridine; t-butyldimethylsiyl triflate / acetonitrile / -30 °C / Inert atmosphere

2.2: 24 h / -30 °C / Inert atmosphere

With 2,6-di-tert-butyl-pyridine; t-butyldimethylsiyl triflate; lithium hexamethyldisilazane; In tetrahydrofuran; acetonitrile; 2.2: Diels-Alder reaction;
DOI:10.1021/ol102798f