(3RS,5S,3'EZ)-3-(4'-iodo-3'-butenyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

Base Information

Chemical Name:(3RS,5S,3'EZ)-3-(4'-iodo-3'-butenyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one
CAS No.:210160-15-9
Molecular Formula:C₁₅H₁₇IO₂S
Molecular Weight:388.269
Hs Code.:

Synonyms:(3RS,5S,3'EZ)-3-(4'-iodo-3'-butenyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

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Chemical Property of (3RS,5S,3'EZ)-3-(4'-iodo-3'-butenyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

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Technology Process of (3RS,5S,3'EZ)-3-(4'-iodo-3'-butenyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

There total 4 articles about (3RS,5S,3'EZ)-3-(4'-iodo-3'-butenyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one 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: 70.0%

: 75-47-8
iodoform

: 210160-17-1
(3RS,5S)-3-(2'-formylethyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

: 210160-15-9
(3RS,5S,3'EZ)-3-(4'-iodo-3'-butenyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

Guidance literature:: With chromium dichloride; In tetrahydrofuran; at 20 ℃; for 8h;
DOI:10.1016/S0040-4020(98)00285-3

Reference yield:

: 184435-75-4
(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one

: 210160-15-9
(3RS,5S,3'EZ)-3-(4'-iodo-3'-butenyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C

1.2: 89 percent / tetrahydrofuran; toluene; hexamethylphosphoric acid triamide / 6 h / 0 - 20 °C

2.1: 96 percent / p-TsOH*H₂O / methanol / 8 h / 20 °C

3.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 20 °C

4.1: 70 percent / CrCl₂ / tetrahydrofuran / 8 h / 20 °C

With chromium dichloride; sodium hexamethyldisilazane; Dess-Martin periodane; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Metallation / 1.2: Alkylation / 2.1: deprotection / 3.1: Dess-Martin oxidation / 4.1: Condensation;
DOI:10.1016/S0040-4020(98)00285-3

Reference yield:

: 191993-23-4
(3RS,5S)-3-(3'-hydroxypropyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

: 210160-15-9
(3RS,5S,3'EZ)-3-(4'-iodo-3'-butenyl)-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 20 °C

2: 70 percent / CrCl₂ / tetrahydrofuran / 8 h / 20 °C

With chromium dichloride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1: Dess-Martin oxidation / 2: Condensation;
DOI:10.1016/S0040-4020(98)00285-3