(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
• Mol file: 1404483-68-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

Dimethylphenylsilane (766-77-8) + (3S,4S)-3-methyl-4-(3-((1R,2R)-2-methylcyclopropyl)prop-2-ynyloxy)-6-(triisopropylsilyloxy)hex-1-en-2-yl acetate (1404483-63-1) → (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 (1404483-68-6)

Guidance literature:

With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; In acetone; for 3h; Inert atmosphere;

DOI:10.1021/ol302744t

Reference yield:

(3S,4R)-4-methyl-1-(triisopropylsilyloxy)-6-(trimethylsilyl)hex-5-yn-3-ol (1404483-53-9) → (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 (1404483-68-6)

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:

(S)-5-chloro-4-methylpentan-2-one (1404483-40-4) → (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 (1404483-68-6)

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

upstream raw materials:

Dimethylphenylsilane

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

1-((1R,2R)-2-methylcyclopropyl)ethanone

3-((1R,2R)-2-methylcyclopropyl)prop-2-ynyl methanesulfonate