(-)-(4R,3S,5S)-4-benzhydryldimethylsilyl-3-butyl-5-dimethylphenylsilylmethyl-2-furanone

Base Information

Chemical Name:(-)-(4R,3S,5S)-4-benzhydryldimethylsilyl-3-butyl-5-dimethylphenylsilylmethyl-2-furanone
CAS No.:333724-15-5
Molecular Formula:C₃₂H₄₂O₂Si₂
Molecular Weight:514.855
Hs Code.:

Synonyms:(-)-(4R,3S,5S)-4-benzhydryldimethylsilyl-3-butyl-5-dimethylphenylsilylmethyl-2-furanone

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Chemical Property of (-)-(4R,3S,5S)-4-benzhydryldimethylsilyl-3-butyl-5-dimethylphenylsilylmethyl-2-furanone

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Technology Process of (-)-(4R,3S,5S)-4-benzhydryldimethylsilyl-3-butyl-5-dimethylphenylsilylmethyl-2-furanone

There total 12 articles about (-)-(4R,3S,5S)-4-benzhydryldimethylsilyl-3-butyl-5-dimethylphenylsilylmethyl-2-furanone 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: 72.0%

: 1189-71-5
isocyanate de chlorosulfonyle

: 333724-14-4
(-)-(S)-(E)-2-(benzhydryldimethylsilyl)-1-dimethylphenylsilyl-3-octene

: 333724-15-5
(-)-(4R,3S,5S)-4-benzhydryldimethylsilyl-3-butyl-5-dimethylphenylsilylmethyl-2-furanone

Guidance literature:: isocyanate de chlorosulfonyle; (-)-(S)-(E)-2-(benzhydryldimethylsilyl)-1-dimethylphenylsilyl-3-octene; In dichloromethane; at 0 ℃; for 2h;

With hydrogenchloride; In tetrahydrofuran; at 22 ℃; for 12h; Further stages.;
DOI:10.1021/ol0069960

Reference yield:

: 132455-95-9
(diphenylmethyl)dimethylchlorosilane

: 333724-15-5
(-)-(4R,3S,5S)-4-benzhydryldimethylsilyl-3-butyl-5-dimethylphenylsilylmethyl-2-furanone

Guidance literature:: Multi-step reaction with 12 steps

1.1: n-BuLi / tetrahydrofuran; various solvent(s) / -78 °C

1.2: tetrahydrofuran; various solvent(s)

2.1: 3.94 g / p-TsOH / methanol / 22 °C

3.1: PCC; NaOAc / CH₂Cl₂ / 4 h / 22 °C

4.1: 71 percent / diethyl ether; various solvent(s) / 3 h / -30 °C

5.1: 91 percent / PDC / CH₂Cl₂ / 12 h / 22 °C

6.1: 99 percent / Noyori's ruthenium catalyst / propan-2-ol / 2 h / 22 °C

7.1: 96 percent / CSA / CH₂Cl₂ / 2 h / 22 °C

8.1: BH₃*DMS; cyclohexene

9.1: 1.38 g / p-TsOH; AcOH

10.1: 98 percent / 18 h / 22 °C

11.1: n-BuLi; CuI; LiCl / various solvent(s)

11.2: 88 percent / tetrahydrofuran; various solvent(s)

12.1: CH₂Cl₂ / 2 h / 0 °C

12.2: 72 percent / aq. HCl / tetrahydrofuran / 12 h / 22 °C

With copper(l) iodide; dipyridinium dichromate; n-butyllithium; dimethylsulfide borane complex; camphor-10-sulfonic acid; sodium acetate; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate; lithium chloride; cyclohexene; Noyori's ruthenium catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; isopropyl alcohol;
DOI:10.1021/ol0069960

Reference yield:

: (benzhydryl-dimethyl-silanyl)-propynal

: 333724-15-5
(-)-(4R,3S,5S)-4-benzhydryldimethylsilyl-3-butyl-5-dimethylphenylsilylmethyl-2-furanone

Guidance literature:: Multi-step reaction with 9 steps

1.1: 71 percent / diethyl ether; various solvent(s) / 3 h / -30 °C

2.1: 91 percent / PDC / CH₂Cl₂ / 12 h / 22 °C

3.1: 99 percent / Noyori's ruthenium catalyst / propan-2-ol / 2 h / 22 °C

4.1: 96 percent / CSA / CH₂Cl₂ / 2 h / 22 °C

5.1: BH₃*DMS; cyclohexene

6.1: 1.38 g / p-TsOH; AcOH

7.1: 98 percent / 18 h / 22 °C

8.1: n-BuLi; CuI; LiCl / various solvent(s)

8.2: 88 percent / tetrahydrofuran; various solvent(s)

9.1: CH₂Cl₂ / 2 h / 0 °C

9.2: 72 percent / aq. HCl / tetrahydrofuran / 12 h / 22 °C

With copper(l) iodide; dipyridinium dichromate; n-butyllithium; dimethylsulfide borane complex; camphor-10-sulfonic acid; toluene-4-sulfonic acid; acetic acid; lithium chloride; cyclohexene; Noyori's ruthenium catalyst; In diethyl ether; dichloromethane; isopropyl alcohol;
DOI:10.1021/ol0069960