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

Base Information

Chemical Name:(2R,4R,5S,1'R)-methanesulfonic acid [5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methyl ester
CAS No.:790662-66-7
Molecular Formula:C₂₉H₅₂O₅SSi₃
Molecular Weight:597.051
Hs Code.:

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

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

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

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

There total 5 articles about (2R,4R,5S,1'R)-methanesulfonic acid [5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methyl ester 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: 99.0%

: 124-63-0
methanesulfonyl chloride

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

: 790662-66-7
(2R,4R,5S,1'R)-methanesulfonic acid [5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.75h;
DOI:10.1021/ol048381z

Reference yield:

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

: 790662-66-7
(2R,4R,5S,1'R)-methanesulfonic acid [5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methyl ester

Guidance literature:: Multi-step reaction with 5 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

5.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0.75 h / 0 °C

With 1H-imidazole; dmap; n-butyllithium; potassium tert-butylate; tin(IV) chloride; diisobutylaluminium hydride; triethylamine; 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

: 790662-66-7
(2R,4R,5S,1'R)-methanesulfonic acid [5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methyl ester

Guidance literature:: Multi-step reaction with 4 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

4: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0.75 h / 0 °C

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