({(1E,3S)-8-(benzyloxy)-1-[(4R,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]oct-1-en-3-yl}oxy)(tert-butyl)(dimethyl)silane

Base Information

• Chemical Name: ({(1E,3S)-8-(benzyloxy)-1-[(4R,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]oct-1-en-3-yl}oxy)(tert-butyl)(dimethyl)silane
• CAS No.: 1608148-72-6
• Molecular Formula: C₃₄H₆₀O₄Si
• Molecular Weight: 560.933

Synonyms:({(1E,3S)-8-(benzyloxy)-1-[(4R,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]oct-1-en-3-yl}oxy)(tert-butyl)(dimethyl)silane

Chemical Property of ({(1E,3S)-8-(benzyloxy)-1-[(4R,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]oct-1-en-3-yl}oxy)(tert-butyl)(dimethyl)silane

Chemical Property:

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Technology Process of ({(1E,3S)-8-(benzyloxy)-1-[(4R,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]oct-1-en-3-yl}oxy)(tert-butyl)(dimethyl)silane

There total 14 articles about ({(1E,3S)-8-(benzyloxy)-1-[(4R,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]oct-1-en-3-yl}oxy)(tert-butyl)(dimethyl)silane 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: 80.0%

t-butyldimethylsiyl triflate (69739-34-0) + (1E,3S)-8-(benzyloxy)-1-[(4R,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]oct-1-en-3-ol (1608148-71-5) → ({(1E,3S)-8-(benzyloxy)-1-[(4R,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]oct-1-en-3-yl}oxy)(tert-butyl)(dimethyl)silane (1608148-72-6)

Guidance literature:

(1E,3S)-8-(benzyloxy)-1-[(4R,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]oct-1-en-3-ol; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.0833333h; Inert atmosphere;

t-butyldimethylsiyl triflate; With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1002/hlca.201300223

Reference yield:

1,6-hexanediol (629-11-8) → ({(1E,3S)-8-(benzyloxy)-1-[(4R,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]oct-1-en-3-yl}oxy)(tert-butyl)(dimethyl)silane (1608148-72-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C

1.2: 20 °C

2.1: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C

3.1: benzene / 0.5 h / Reflux

4.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.5 h / -10 - 0 °C

5.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 0.5 h / -30 °C / Molecular sieve

5.2: 4 h / -30 °C / Molecular sieve

6.1: 1H-imidazole; triphenylphosphine; iodine / tetrahydrofuran / 1.08 h / 0 - 20 °C

7.1: zinc / methanol / 6 h / Reflux

8.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

9.2: 0.17 h / 0 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) isopropylate; oxalyl dichloride; diethyl (2S,3S)-tartrate; iodine; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; In tetrahydrofuran; methanol; dichloromethane; toluene; mineral oil; benzene; 2.1: |Swern Oxidation / 3.1: |Wittig Olefination / 5.1: |Sharpless Asymmetric Epoxidation / 5.2: |Sharpless Asymmetric Epoxidation;

DOI:10.1002/hlca.201300223

Reference yield:

(1R)-1-[(4S,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]-2-[(methylsulfonyl)oxy]ethyl methanesulfonate (1608148-68-0) → ({(1E,3S)-8-(benzyloxy)-1-[(4R,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]oct-1-en-3-yl}oxy)(tert-butyl)(dimethyl)silane (1608148-72-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium iodide; zinc / N,N-dimethyl-formamide / 8 h / 90 °C

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

3.2: 0.17 h / 0 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.201300223

upstream raw materials:

t-butyldimethylsiyl triflate

(1E,3S)-8-(benzyloxy)-1-[(4R,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]oct-1-en-3-ol

(1R)-1-{(4R,5S)-2,2-dimethyl-5-oct-1-en-1-yl-1,3-dioxolan-4-yl}ethane-1,2-diol

(1R)-1-[(4R,5S)-2,2-dimethyl-5-octyl-1,3-dioxolan-4-yl]ethane-1,2-diol

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