(3S,4S)-4-(((Z)-3-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-methylcyclopropyl)allyl)oxy)-3-methyl-6-((triisopropylsilyl)oxy)hex-1-en-2-yl acetate

Base Information

Chemical Name:(3S,4S)-4-(((Z)-3-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-methylcyclopropyl)allyl)oxy)-3-methyl-6-((triisopropylsilyl)oxy)hex-1-en-2-yl acetate
CAS No.:1404483-68-6
Molecular Formula:C₃₃H₅₆O₄Si₂
Molecular Weight:572.976
Hs Code.:

Synonyms:(3S,4S)-4-(((Z)-3-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-methylcyclopropyl)allyl)oxy)-3-methyl-6-((triisopropylsilyl)oxy)hex-1-en-2-yl acetate

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Chemical Property of (3S,4S)-4-(((Z)-3-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-methylcyclopropyl)allyl)oxy)-3-methyl-6-((triisopropylsilyl)oxy)hex-1-en-2-yl acetate

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Technology Process of (3S,4S)-4-(((Z)-3-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-methylcyclopropyl)allyl)oxy)-3-methyl-6-((triisopropylsilyl)oxy)hex-1-en-2-yl acetate

There total 7 articles about (3S,4S)-4-(((Z)-3-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-methylcyclopropyl)allyl)oxy)-3-methyl-6-((triisopropylsilyl)oxy)hex-1-en-2-yl acetate 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: 71.0%

: 766-77-8
Dimethylphenylsilane

: 1404483-63-1
(3S,4S)-3-methyl-4-(3-((1R,2R)-2-methylcyclopropyl)prop-2-ynyloxy)-6-(triisopropylsilyloxy)hex-1-en-2-yl acetate

: 1404483-68-6
(3S,4S)-4-(((Z)-3-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-methylcyclopropyl)allyl)oxy)-3-methyl-6-((triisopropylsilyl)oxy)hex-1-en-2-yl acetate

Guidance literature:: With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; In acetone; for 3h; Inert atmosphere;
DOI:10.1021/ol302744t

Reference yield:

: 1404483-53-9
(3S,4R)-4-methyl-1-(triisopropylsilyloxy)-6-(trimethylsilyl)hex-5-yn-3-ol

: 1404483-68-6
(3S,4S)-4-(((Z)-3-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-methylcyclopropyl)allyl)oxy)-3-methyl-6-((triisopropylsilyl)oxy)hex-1-en-2-yl acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 15-crown-5 / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; sodium carbonate; trifuran-2-yl-phosphane / toluene / 80 °C / Inert atmosphere

3.1: cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate / acetone / 3 h / Inert atmosphere

With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; trifuran-2-yl-phosphane; 15-crown-5; sodium carbonate; In tetrahydrofuran; acetone; toluene;
DOI:10.1021/ol302744t

Reference yield:

: 1404483-40-4
(S)-5-chloro-4-methylpentan-2-one

: 1404483-68-6
(3S,4S)-4-(((Z)-3-(dimethyl(phenyl)silyl)-3-((1R,2R)-2-methylcyclopropyl)allyl)oxy)-3-methyl-6-((triisopropylsilyl)oxy)hex-1-en-2-yl acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydroxide / water / 80 °C / Inert atmosphere

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

2.2: 0.5 h / 0 - 20 °C / Inert atmosphere

2.3: 1 h / Reflux; Inert atmosphere

3.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: 15-crown-5 / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; sodium carbonate; trifuran-2-yl-phosphane / toluene / 80 °C / Inert atmosphere

6.1: cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate / acetone / 3 h / Inert atmosphere

With n-butyllithium; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; trifuran-2-yl-phosphane; 15-crown-5; sodium carbonate; triethylamine; diisopropylamine; sodium hydroxide; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene;
DOI:10.1021/ol302744t