(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

Base Information

• Chemical Name: (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
• CAS No.: 790662-70-3
• Molecular Formula: C₅₁H₈₂O₇S₂Si₂
• Molecular Weight: 927.511

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

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Technology Process of (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

There total 13 articles about (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 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:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + benzaldehyde (100-52-7) + (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 (790662-61-2) → (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 (790662-70-3)

Guidance literature:

benzaldehyde; (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; With samarium diiodide; In tetrahydrofuran; at -10 ℃; for 0.25h;

triisopropylsilyl trifluoromethanesulfonate; With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20 ℃; for 6h;

DOI:10.1021/ol048381z

Reference yield:

(2R,4R,5S,1'R)-[5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol (790662-52-1) → (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 (790662-70-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0.75 h / 0 °C

2.1: 94 percent / NaI / acetone / 48 h / 75 °C

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

3.2: 12 mg / t-BuOK; TBAF / dimethylsulfoxide; H₂O; tetrahydrofuran / 4 h / 95 °C

4.1: TBAF / dimethylformamide; tetrahydrofuran / 80 °C

5.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 - 20 °C

6.1: 97 percent / phosphate buffer; DDQ / CH₂Cl₂ / 0 - 20 °C / pH 7

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

8.1: 93 percent / Cy₂BCl; Et₃N / diethyl ether; hexane / 0.42 h / -78 °C

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

9.2: 0.013 mg / 2,6-lutidine / CH₂Cl₂ / 6 h / -78 - 20 °C

With 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; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ol048381z

Reference yield:

(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) → (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 (790662-70-3)

Guidance literature:

Multi-step reaction with 10 steps

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

2.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0.75 h / 0 °C

3.1: 94 percent / NaI / acetone / 48 h / 75 °C

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

4.2: 12 mg / t-BuOK; TBAF / dimethylsulfoxide; H₂O; tetrahydrofuran / 4 h / 95 °C

5.1: TBAF / dimethylformamide; tetrahydrofuran / 80 °C

6.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 - 20 °C

7.1: 97 percent / phosphate buffer; DDQ / CH₂Cl₂ / 0 - 20 °C / pH 7

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

9.1: 93 percent / Cy₂BCl; Et₃N / diethyl ether; hexane / 0.42 h / -78 °C

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

10.2: 0.013 mg / 2,6-lutidine / CH₂Cl₂ / 6 h / -78 - 20 °C

With 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; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ol048381z

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

benzaldehyde

(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

t-butyldimethylsiyl triflate

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

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