(2R,4R,5S,1'R)-[5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol

Base Information

Chemical Name:(2R,4R,5S,1'R)-[5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol
CAS No.:790662-52-1
Molecular Formula:C₂₈H₅₀O₃Si₃
Molecular Weight:518.96
Hs Code.:

Synonyms:(2R,4R,5S,1'R)-[5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol

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Chemical Property of (2R,4R,5S,1'R)-[5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol

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Technology Process of (2R,4R,5S,1'R)-[5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol

There total 4 articles about (2R,4R,5S,1'R)-[5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol 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:

: 790662-51-0
(2R,4R,5S,1'R)-5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carboxylic acid ethyl ester

: 790662-52-1
(2R,4R,5S,1'R)-[5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; at 0 ℃; for 2.5h;
DOI:10.1021/ol048381z

Reference yield:

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

: 790662-52-1
(2R,4R,5S,1'R)-[5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / -78 - -45 °C

1.2: (-)-Ipc₂BOMe; BF₃*OEt₂ / tetrahydrofuran; hexane / 6 h / -78 °C

1.3: KH₂PO₄; KOH; H₂O₂ / tetrahydrofuran; hexane; H₂O / 1 h / 20 °C

2.1: 82 percent / imidazole / dimethylformamide / 16 h

3.1: 62 percent / SnCl₄ / toluene; CH₂Cl₂ / 0.75 h / -78 °C

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

With 1H-imidazole; n-butyllithium; potassium tert-butylate; tin(IV) chloride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol048381z

Reference yield:

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

: 790662-52-1
(2R,4R,5S,1'R)-[5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / imidazole / dimethylformamide / 16 h

2: 62 percent / SnCl₄ / toluene; CH₂Cl₂ / 0.75 h / -78 °C

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

With 1H-imidazole; tin(IV) chloride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol048381z