2-(6-Acetoxy-3-oxo-3,6-dihydro-2H-pyran-2-ylmethyl)-2-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-malonic acid diethyl ester

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Chemical Name:2-(6-Acetoxy-3-oxo-3,6-dihydro-2H-pyran-2-ylmethyl)-2-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-malonic acid diethyl ester
CAS No.:475296-47-0
Molecular Formula:C₂₅H₃₀O₉S
Molecular Weight:506.574
Hs Code.:

Synonyms:2-(6-Acetoxy-3-oxo-3,6-dihydro-2H-pyran-2-ylmethyl)-2-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-malonic acid diethyl ester

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Chemical Property of 2-(6-Acetoxy-3-oxo-3,6-dihydro-2H-pyran-2-ylmethyl)-2-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-malonic acid diethyl ester

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Technology Process of 2-(6-Acetoxy-3-oxo-3,6-dihydro-2H-pyran-2-ylmethyl)-2-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-malonic acid diethyl ester

There total 9 articles about 2-(6-Acetoxy-3-oxo-3,6-dihydro-2H-pyran-2-ylmethyl)-2-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-malonic acid diethyl ester 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:

: 2-((S)-6-Hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-ylmethyl)-2-[(E)-3-((S)-toluene-4-sulfinyl)-allyl]-malonic acid diethyl ester

: 75-36-5
acetyl chloride

: 475296-47-0
2-(6-Acetoxy-3-oxo-3,6-dihydro-2H-pyran-2-ylmethyl)-2-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-malonic acid diethyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/ol026633v

Reference yield:

: 23193-16-0
2-(2-oxoethyl)malonic acid diethyl ester

: 475296-47-0
2-(6-Acetoxy-3-oxo-3,6-dihydro-2H-pyran-2-ylmethyl)-2-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-malonic acid diethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran / 0.5 h / 0 °C

1.2: tetrahydrofuran / 0.17 h / -78 °C

2.1: 2.40 g / Et₃H / 0.5 h / -78 °C

3.1: NaH / tetrahydrofuran / 0.33 h / 30 °C

3.2: 93 percent / tetrahydrofuran / 0.5 h / 20 °C

4.1: TBAF; acetic acid / tetrahydrofuran / 0.33 h / 0 °C

4.2: N-bromosuccinimide / tetrahydrofuran; H₂O / 0.33 h / 0 °C

5.1: Et₃N; DMAP / CH₂Cl₂ / 0.5 h / -78 °C

With dmap; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol026633v

Reference yield:

: 2-(2-furan-2-yl-2-hydroxy-ethyl)-malonic acid diethyl ester

: 475296-47-0
2-(6-Acetoxy-3-oxo-3,6-dihydro-2H-pyran-2-ylmethyl)-2-[(E)-3-((R)-toluene-4-sulfinyl)-allyl]-malonic acid diethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2.40 g / Et₃H / 0.5 h / -78 °C

2.1: NaH / tetrahydrofuran / 0.33 h / 30 °C

2.2: 93 percent / tetrahydrofuran / 0.5 h / 20 °C

3.1: TBAF; acetic acid / tetrahydrofuran / 0.33 h / 0 °C

3.2: N-bromosuccinimide / tetrahydrofuran; H₂O / 0.33 h / 0 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 0.5 h / -78 °C

With dmap; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol026633v