(6R)-6-[(2R)-(2-methyl-4-phenylsulfanyl-butyl)]-5,6-dihydro-2H-pyran-2-one

Base Information

Chemical Name:(6R)-6-[(2R)-(2-methyl-4-phenylsulfanyl-butyl)]-5,6-dihydro-2H-pyran-2-one
CAS No.:385809-09-6
Molecular Formula:C₁₆H₂₀O₂S
Molecular Weight:276.4
Hs Code.:

Synonyms:(6R)-6-[(2R)-(2-methyl-4-phenylsulfanyl-butyl)]-5,6-dihydro-2H-pyran-2-one

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Chemical Property of (6R)-6-[(2R)-(2-methyl-4-phenylsulfanyl-butyl)]-5,6-dihydro-2H-pyran-2-one

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Technology Process of (6R)-6-[(2R)-(2-methyl-4-phenylsulfanyl-butyl)]-5,6-dihydro-2H-pyran-2-one

There total 11 articles about (6R)-6-[(2R)-(2-methyl-4-phenylsulfanyl-butyl)]-5,6-dihydro-2H-pyran-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: 88.0%

: 38435-08-4
trimethyl 3-(phenylsulfonyl)orthopropionate

: 385809-08-5
(2R)-2-[(2R)-(2-methyl-4-phenylsullfanyl-butyl)]oxirane

: 385809-09-6
(6R)-6-[(2R)-(2-methyl-4-phenylsulfanyl-butyl)]-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multistep reaction;
DOI:10.1002/1521-3773(20011015)40:20<3842::AID-ANIE3842>3.0.CO;2-R

Reference yield:

: 89408-85-5
(S)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one

: 385809-09-6
(6R)-6-[(2R)-(2-methyl-4-phenylsulfanyl-butyl)]-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 89 percent / imidazole; DMAP / CH₂Cl₂; toluene / 16 h / 0 - 20 °C

2.1: CuI / 0 °C

2.2: 84 percent / diethyl ether / 1 h / 0 °C

3.1: 98 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

4.1: 83 percent / Bu₃P / tetrahydrofuran / 16 h / 0 - 20 °C

5.1: Et₃N / CH₂Cl₂ / 1 h / -10 °C

6.1: TBAF / tetrahydrofuran / 1 h / 0 - 5 °C

6.2: 812 mg / aq. NaOH / tetrahydrofuran / 0.75 h / 0 - 5 °C

7.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 1.5 h / -78 °C

7.2: aq. TFA / 3 h / 20 °C

7.3: 88 percent / DBU / CH₂Cl₂ / 0.5 h / 0 - 5 °C

With 1H-imidazole; dmap; copper(l) iodide; lithium borohydride; n-butyllithium; tributylphosphine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/jo026743f

Reference yield:

: 527742-73-0
(6S)-6-(tert-butyldimethylsilanyloxymethyl)-5,6-dihydro-2H-pyran-2-one

: 385809-09-6
(6R)-6-[(2R)-(2-methyl-4-phenylsulfanyl-butyl)]-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: CuI / 0 °C

1.2: 84 percent / diethyl ether / 1 h / 0 °C

2.1: 98 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

3.1: 83 percent / Bu₃P / tetrahydrofuran / 16 h / 0 - 20 °C

4.1: Et₃N / CH₂Cl₂ / 1 h / -10 °C

5.1: TBAF / tetrahydrofuran / 1 h / 0 - 5 °C

5.2: 812 mg / aq. NaOH / tetrahydrofuran / 0.75 h / 0 - 5 °C

6.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 1.5 h / -78 °C

6.2: aq. TFA / 3 h / 20 °C

6.3: 88 percent / DBU / CH₂Cl₂ / 0.5 h / 0 - 5 °C

With copper(l) iodide; lithium borohydride; n-butyllithium; tributylphosphine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo026743f