Toluene-4-sulfonic acid (S)-2-{(2S,5R,2'S,5'R)-5'-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-tridec-12-enyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

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Chemical Name:Toluene-4-sulfonic acid (S)-2-{(2S,5R,2'S,5'R)-5'-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-tridec-12-enyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester
CAS No.:749917-49-5
Molecular Formula:C₃₆H₆₂O₇SSi
Molecular Weight:667.036
Hs Code.:

Toluene-4-sulfonic acid (S)-2-{(2S,5R,2'S,5'R)-5'-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-tridec-12-enyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

Synonyms:Toluene-4-sulfonic acid (S)-2-{(2S,5R,2'S,5'R)-5'-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-tridec-12-enyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

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Chemical Property of Toluene-4-sulfonic acid (S)-2-{(2S,5R,2'S,5'R)-5'-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-tridec-12-enyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

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Technology Process of Toluene-4-sulfonic acid (S)-2-{(2S,5R,2'S,5'R)-5'-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-tridec-12-enyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

There total 15 articles about Toluene-4-sulfonic acid (S)-2-{(2S,5R,2'S,5'R)-5'-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-tridec-12-enyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-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: 99.0%

: 98-59-9
p-toluenesulfonyl chloride

: 749917-48-4
(S)-1-{(2S,5R,2'S,5'R)-5'-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-tridec-12-enyl]-octahydro-[2,2']bifuranyl-5-yl}-ethane-1,2-diol

: 749917-49-5
Toluene-4-sulfonic acid (S)-2-{(2S,5R,2'S,5'R)-5'-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-tridec-12-enyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

Guidance literature:: With tetrabutylammomium bromide; di(n-butyl)tin oxide; In benzene;
DOI:10.1055/s-2004-825624

Reference yield:

: 88476-93-1
10-undecen-1-ylmagnesium bromide

: 749917-49-5
Toluene-4-sulfonic acid (S)-2-{(2S,5R,2'S,5'R)-5'-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-tridec-12-enyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / CuI / tetrahydrofuran / -50 °C

2: 80 percent / imidazole / CH₂Cl₂

3: 99 percent / DIBALH / tetrahydrofuran

4: 99 percent / toluene

5: 89 percent / DIBALH / tetrahydrofuran

6: 86 percent / L-(+)-DET; Ti(O-i-Pr)4; t-BuOOH / 4 Angstroem molecular sieves / CH₂Cl₂

7: 99 percent / Bu₂SnO; TBAB / benzene

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; diethyl (2R,3R)-tartrate; tetrabutylammomium bromide; diisobutylaluminium hydride; di(n-butyl)tin oxide; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; toluene; benzene; 6: Sharpless asymmetric epoxidation;
DOI:10.1055/s-2004-825624

Reference yield:

: 197968-20-0
diethyl (2E,6E,10E)-3,10-dodeca-2,6,10-trienedioate

: 749917-49-5
Toluene-4-sulfonic acid (S)-2-{(2S,5R,2'S,5'R)-5'-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-tridec-12-enyl]-octahydro-[2,2']bifuranyl-5-yl}-2-hydroxy-ethyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 83 percent / aq. NaOH; NaHCO₃ / methanol / 80 °C

2.1: (COCl)2 / dimethylformamide; CH₂Cl₂

3.1: NaH / tetrahydrofuran

4.1: KMnO₄; adogen 464 / acetone; acetic acid

4.2: 76 percent / NaIO₄-SiO₂ / CH₂Cl₂

5.1: BH₃*SMe₂; NaBH₄ / tetrahydrofuran

6.1: Bu₂SnO; TBAB / benzene

7.1: DBU / CH₂Cl₂

8.1: 82 percent / CuI / tetrahydrofuran / -50 °C

9.1: 80 percent / imidazole / CH₂Cl₂

10.1: 99 percent / DIBALH / tetrahydrofuran

11.1: 99 percent / toluene

12.1: 89 percent / DIBALH / tetrahydrofuran

13.1: 86 percent / L-(+)-DET; Ti(O-i-Pr)4; t-BuOOH / 4 Angstroem molecular sieves / CH₂Cl₂

14.1: 99 percent / Bu₂SnO; TBAB / benzene

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; sodium tetrahydroborate; potassium permanganate; copper(l) iodide; oxalyl dichloride; adogen 464; diethyl (2R,3R)-tartrate; dimethylsulfide borane complex; tetrabutylammomium bromide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; toluene; benzene; 13.1: Sharpless asymmetric epoxidation;
DOI:10.1055/s-2004-825624