(3R,4S)-4-(dimethylphenylsilanyl)-1-(triethylsilanyl)hex-5-en-1-yn-3-ol

Base Information

Chemical Name:(3R,4S)-4-(dimethylphenylsilanyl)-1-(triethylsilanyl)hex-5-en-1-yn-3-ol
CAS No.:790662-65-6
Molecular Formula:C₂₀H₃₂OSi₂
Molecular Weight:344.644
Hs Code.:

Synonyms:(3R,4S)-4-(dimethylphenylsilanyl)-1-(triethylsilanyl)hex-5-en-1-yn-3-ol

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Chemical Property of (3R,4S)-4-(dimethylphenylsilanyl)-1-(triethylsilanyl)hex-5-en-1-yn-3-ol

Chemical Property:

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Technology Process of (3R,4S)-4-(dimethylphenylsilanyl)-1-(triethylsilanyl)hex-5-en-1-yn-3-ol

There total 1 articles about (3R,4S)-4-(dimethylphenylsilanyl)-1-(triethylsilanyl)hex-5-en-1-yn-3-ol 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:

: 18001-18-8
allyldimethylphenylsilane

: 71572-60-6
3-triethylsilyl-2-propynal

: (3S,4R)-4-(dimethylphenylsilanyl)-1-(triethylsilanyl)hex-5-en-1-yn-3-ol

: 790662-65-6
(3R,4S)-4-(dimethylphenylsilanyl)-1-(triethylsilanyl)hex-5-en-1-yn-3-ol

Guidance literature:: allyldimethylphenylsilane; With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane; at -78 - -45 ℃;

3-triethylsilyl-2-propynal; With boron trifluoride diethyl etherate; (-)-B-methoxydiisopinocampheylborane; In tetrahydrofuran; hexane; at -78 ℃; for 6h;

With potassium hydroxide; potassium dihydrogenphosphate; dihydrogen peroxide; In tetrahydrofuran; hexane; water; at 20 ℃; for 1h; Title compound not separated from byproducts;
DOI:10.1021/ol048381z

Reference yield: 82.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 790662-65-6
(3R,4S)-4-(dimethylphenylsilanyl)-1-(triethylsilanyl)hex-5-en-1-yn-3-ol

: 790662-50-9
(1S,2R)-{[2-(tert-butyldimethylsilanyloxy)-4-(triethylsilanyl)-1-vinylbut-3-ynyl]dimethylsilanyl}benzene

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 16h;
DOI:10.1021/ol048381z

Reference yield:

: 790662-65-6
(3R,4S)-4-(dimethylphenylsilanyl)-1-(triethylsilanyl)hex-5-en-1-yn-3-ol

: Benzoic acid (1S,3S,4R)-1-[(S)-2-(2-{(2R,5R)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-2-iodo-allyl]-tetrahydro-furan-2-ylmethyl}-[1,3]dithian-2-yl)-1-methyl-ethyl]-5-(4-methoxy-benzyloxy)-4-methyl-3-triisopropylsilanyloxy-pentyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 82 percent / imidazole / dimethylformamide / 16 h

2.1: 62 percent / SnCl₄ / toluene; CH₂Cl₂ / 0.75 h / -78 °C

3.1: DIBAL-H / tetrahydrofuran; CH₂Cl₂ / 2.5 h / 0 °C

4.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0.75 h / 0 °C

5.1: 94 percent / NaI / acetone / 48 h / 75 °C

6.1: HMPA; t-BuLi / tetrahydrofuran / 0.75 h / -78 °C

6.2: 12 mg / t-BuOK; TBAF / dimethylsulfoxide; H₂O; tetrahydrofuran / 4 h / 95 °C

7.1: TBAF / dimethylformamide; tetrahydrofuran / 80 °C

8.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 - 20 °C

9.1: 97 percent / phosphate buffer; DDQ / CH₂Cl₂ / 0 - 20 °C / pH 7

10.1: iPr₂NEt; DMSO; SO₃*Pyr / CH₂Cl₂ / 0.25 h / 0 °C

11.1: 93 percent / Cy₂BCl; Et₃N / diethyl ether; hexane / 0.42 h / -78 °C

12.1: SmI₂ / tetrahydrofuran / 0.25 h / -10 °C

12.2: 0.013 mg / 2,6-lutidine / CH₂Cl₂ / 6 h / -78 - 20 °C

13.1: n-Bu₃SnH / PdCl₂(PPh₃)2 / tetrahydrofuran / 2 h / 0 °C

13.2: I₂ / CH₂Cl₂ / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; phosphate buffer; samarium diiodide; pyridine-SO₃ complex; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; tri-n-butyl-tin hydride; tin(IV) chloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/ol048381z