(3S,4R)-4-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-hydroxy-3,3-dimethylcyclobutyl)dihydrofuran-2(3H)-one

Base Information

Chemical Name:(3S,4R)-4-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-hydroxy-3,3-dimethylcyclobutyl)dihydrofuran-2(3H)-one
CAS No.:1256752-96-1
Molecular Formula:C₁₈H₂₆O₃Si
Molecular Weight:318.488
Hs Code.:

Synonyms:(3S,4R)-4-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-hydroxy-3,3-dimethylcyclobutyl)dihydrofuran-2(3H)-one

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Chemical Property of (3S,4R)-4-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-hydroxy-3,3-dimethylcyclobutyl)dihydrofuran-2(3H)-one

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Technology Process of (3S,4R)-4-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-hydroxy-3,3-dimethylcyclobutyl)dihydrofuran-2(3H)-one

There total 8 articles about (3S,4R)-4-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-hydroxy-3,3-dimethylcyclobutyl)dihydrofuran-2(3H)-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:

: 1256752-95-0
(R,Z)-4-(4-(dimethylphenylsilyl)-2-oxodihydrofuran-3(2H)-ylidene)-2,2-dimethylbutanal

: (3S,4R)-4-(dimethyl(phenyl)silyl)-3-((1S,2S)-2-hydroxy-3,3-dimethylcyclobutyl) dihydrofuran-2(3H)-one

: 1256752-96-1
(3S,4R)-4-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-hydroxy-3,3-dimethylcyclobutyl)dihydrofuran-2(3H)-one

Guidance literature:: With methanol; samarium diiodide; In tetrahydrofuran; at 0 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol102278c

Reference yield:

: C₂₁H₃₀O₂S₂Si

: (3S,4R)-4-(dimethyl(phenyl)silyl)-3-((1S,2S)-2-hydroxy-3,3-dimethylcyclobutyl) dihydrofuran-2(3H)-one

: 1256752-96-1
(3S,4R)-4-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-hydroxy-3,3-dimethylcyclobutyl)dihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 2 steps

1: water; calcium carbonate; methyl iodide / acetonitrile / 60 °C / Inert atmosphere

2: methanol; samarium diiodide / tetrahydrofuran / 0 °C / Inert atmosphere

With methanol; samarium diiodide; water; calcium carbonate; methyl iodide; In tetrahydrofuran; acetonitrile;
DOI:10.1021/ol102278c

Reference yield:

: 156600-00-9
(R)-1-(dimethyl(phenyl)silyl)ethane-1,2-diol

: (3S,4R)-4-(dimethyl(phenyl)silyl)-3-((1S,2S)-2-hydroxy-3,3-dimethylcyclobutyl) dihydrofuran-2(3H)-one

: 1256752-96-1
(3S,4R)-4-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-hydroxy-3,3-dimethylcyclobutyl)dihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: Trimethyl orthoacetate; chloro-trimethyl-silane; pyridinium p-toluenesulfonate / dichloromethane / 4 h / Inert atmosphere

1.2: Inert atmosphere

2.1: copper(l) iodide / diethyl ether / 0.33 h / -45 °C / Inert atmosphere

2.2: 3 h / Inert atmosphere

3.1: potassium osmate(VI) dihydrate / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere

3.2: 3 h / 20 °C / Inert atmosphere

3.3: 1 h / 0 °C / Inert atmosphere

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: 24 h / -78 °C / Inert atmosphere

5.1: methanesulfonyl chloride; triethylamine / dichloromethane / 20 - 35 °C / Inert atmosphere

6.1: water; calcium carbonate; methyl iodide / acetonitrile / 60 °C / Inert atmosphere

7.1: methanol; samarium diiodide / tetrahydrofuran / 0 °C / Inert atmosphere

With methanol; Trimethyl orthoacetate; potassium osmate(VI) dihydrate; copper(l) iodide; n-butyllithium; chloro-trimethyl-silane; samarium diiodide; water; pyridinium p-toluenesulfonate; methanesulfonyl chloride; triethylamine; diisopropylamine; calcium carbonate; methyl iodide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol102278c