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

Base Information

• Chemical Name: (2R,4R,3S,1'R)-2-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-3-(dimethylphenylsilanyl)-5-iodomethyltetrahydrofuran
• CAS No.: 790662-53-2
• Molecular Formula: C₂₈H₄₉IO₂Si₃
• Molecular Weight: 628.857

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (2R,4R,3S,1'R)-2-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-3-(dimethylphenylsilanyl)-5-iodomethyltetrahydrofuran 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: 94.0%

(2R,4R,5S,1'R)-methanesulfonic acid [5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methyl ester (790662-66-7) → (2R,4R,3S,1'R)-2-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-3-(dimethylphenylsilanyl)-5-iodomethyltetrahydrofuran (790662-53-2)

Guidance literature:

With sodium iodide; In acetone; at 75 ℃; for 48h;

DOI:10.1021/ol048381z

Reference yield:

3-triethylsilyl-2-propynal (71572-60-6) → (2R,4R,3S,1'R)-2-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-3-(dimethylphenylsilanyl)-5-iodomethyltetrahydrofuran (790662-53-2)

Guidance literature:

Multi-step reaction with 6 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

6.1: 94 percent / NaI / acetone / 48 h / 75 °C

With 1H-imidazole; dmap; n-butyllithium; potassium tert-butylate; tin(IV) chloride; diisobutylaluminium hydride; triethylamine; sodium iodide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ol048381z

Reference yield:

(3R,4S)-4-(dimethylphenylsilanyl)-1-(triethylsilanyl)hex-5-en-1-yn-3-ol (790662-65-6) → (2R,4R,3S,1'R)-2-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-3-(dimethylphenylsilanyl)-5-iodomethyltetrahydrofuran (790662-53-2)

Guidance literature:

Multi-step reaction with 5 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

5: 94 percent / NaI / acetone / 48 h / 75 °C

With 1H-imidazole; dmap; tin(IV) chloride; diisobutylaluminium hydride; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/ol048381z

upstream raw materials:

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

3-triethylsilyl-2-propynal

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

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

Downstream raw materials:

(2S,3R,5R,2'S,1''R)-1''-(3-(hydroxydimethylsilanyl)-5-{2-[3'-(4-methoxybenzyloxy)-2'-methylpropyl][1,3]dithian-2-ylmethyl}tetrahydrofuran-2-yl)prop-2''-yn-1''-ol

(1S,3S,4R,1'S,2''R,5''R,1'''R,E)-benzoic acid 1-[2'-(2-{5''-[1'''-(tert-butyldimethylsilyloxy)-3'''-iodoallyl]tetrahydrofuran-2''-ylmethyl}-[1,3]dithian-2-yl)-1'-methylethyl]-3-hydroxy-5-(4-methoxybenzyloxy)-4-methyl-3-(triisopropylsilyloxy)pentyl ester

(2S,3R,5R,1'R,2''S)-2-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-3-(dimethylphenylsilanyl)-5-{2-[3''-(4-methoxybenzyloxy)-2''-methylpropyl][1,3]dithian-2-ylmethyl}tetrahydrofuran

(2S,3R,5R,2'S,1''R)-1''-{(3-(dimethylphenylsilanyl)-5-{2-[3'-(4-methoxybenzyloxy)-2'-methylpropyl][1,3]dithian-2-ylmethyl}tetrahydrofuran-2-yl)}prop-2''-yn-1''-ol

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