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

Base Information

• Chemical Name: (2R,4R,5S,1'R)-5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carboxylic acid ethyl ester
• CAS No.: 790662-51-0
• Molecular Formula: C₃₀H₅₂O₄Si₃
• Molecular Weight: 560.997

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (2R,4R,5S,1'R)-5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carboxylic acid ethyl 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: 62.0%

glyoxylic acid ethyl ester (924-44-7) + (1S,2R)-{[2-(tert-butyldimethylsilanyloxy)-4-(triethylsilanyl)-1-vinylbut-3-ynyl]dimethylsilanyl}benzene (790662-50-9) → (2R,4R,5S,1'R)-5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carboxylic acid ethyl ester (790662-51-0)

Guidance literature:

With tin(IV) chloride; In dichloromethane; toluene; at -78 ℃; for 0.75h;

DOI:10.1021/ol048381z

Reference yield:

3-triethylsilyl-2-propynal (71572-60-6) → (2R,4R,5S,1'R)-5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carboxylic acid ethyl ester (790662-51-0)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; n-butyllithium; potassium tert-butylate; tin(IV) chloride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 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,5S,1'R)-5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carboxylic acid ethyl ester (790662-51-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / imidazole / dimethylformamide / 16 h

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

With 1H-imidazole; tin(IV) chloride; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol048381z

upstream raw materials:

glyoxylic acid ethyl ester

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

3-triethylsilyl-2-propynal

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

Downstream raw materials:

(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

(1S,3S,4R,1'S,2''R,5''R,1'''R)-benzoic acid 1-[2'-(2-{5''-[1'''-(tert-butyldimethylsilanyloxy)prop-2'''-ynyl]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

(2R,5S,6S,2'R,5'R,1''R)-7-(2-{5'-[1''-(tert-butyldimethylsilanyloxy)prop-2''-ynyl]tetrahydrofuran-2'-ylmethyl}-[1,3]dithian-2-yl)-5-hydroxy-1-(4-methoxybenzyloxy)-2,6-dimethylheptan-3-one

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