Toluene-4-sulfonic acid (S)-2-{(2R,5S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-2-hydroxy-propyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (S)-2-{(2R,5S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-2-hydroxy-propyl ester
CAS No.:90461-01-1
Molecular Formula:C₃₃H₄₄O₆SSi
Molecular Weight:596.86
Hs Code.:

Toluene-4-sulfonic acid (S)-2-{(2R,5S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-2-hydroxy-propyl ester

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Chemical Property of Toluene-4-sulfonic acid (S)-2-{(2R,5S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-2-hydroxy-propyl ester

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Technology Process of Toluene-4-sulfonic acid (S)-2-{(2R,5S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-2-hydroxy-propyl ester

There total 13 articles about Toluene-4-sulfonic acid (S)-2-{(2R,5S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-2-hydroxy-propyl 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:

: Acetic acid (1E,3Z,5E)-7-hydroxy-2,6-dimethyl-hepta-1,3,5-trienyl ester

: 90461-01-1
Toluene-4-sulfonic acid (S)-2-{(2R,5S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-2-hydroxy-propyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 50 percent / 1.) Ti(O-i-Pr)4, (-)-Diethyl D-tartrate, t-BuOOH, / CH₂Cl₂ / -15 °C

2: 94.7 percent / Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

3: 94 percent / 5percent HClO₄ / acetonitrile / 4 h / Ambient temperature

4: 90 percent / Phosphorus oxychloride / CH₂Cl₂ / 24 h / Ambient temperature

5: 90 percent / K₂CO₃ / methanol / 1 h / 0 °C

6: 83 percent / Dowex H⁺ / methanol / 24 h / Ambient temperature

7: 60 percent / 1.) Ti(O-i-Pr), (-)-Diethyl D-tatrate, t-BuOOH, 2.) Tattratic acid / CH₂Cl₂ / 1.) -23 degC, 30 min. 2.) stirring

8: 82.5 percent / pyridine / 0 °C / overnight

9: NaI / butan-2-one / 3 h / Heating

10: 98.4 percent / Tri-n-butyltin hydride / ethanol / 2 h / Ambient temperature

11: Imidazole / dimethylformamide / 3 h / 60 °C

12: 95.3 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

13: pyridine / 0 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; perchloric acid; diethyl (2S,3S)-tartrate; Dowex H⁺; Tattratic acid; tri-n-butyl-tin hydride; potassium carbonate; (-)-diethyl tartrate; triethylamine; sodium iodide; trichlorophosphate; In pyridine; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; butanone;
DOI:10.1021/jo00188a014

Reference yield:

: 90460-97-2
(S)-4-((E)-(R)-1,6-Dihydroxy-4-methyl-hex-4-enyl)-4-methyl-[1,3]dioxolan-2-one

: 90461-01-1
Toluene-4-sulfonic acid (S)-2-{(2R,5S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-2-hydroxy-propyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 60 percent / 1.) Ti(O-i-Pr), (-)-Diethyl D-tatrate, t-BuOOH, 2.) Tattratic acid / CH₂Cl₂ / 1.) -23 degC, 30 min. 2.) stirring

2: 82.5 percent / pyridine / 0 °C / overnight

3: NaI / butan-2-one / 3 h / Heating

4: 98.4 percent / Tri-n-butyltin hydride / ethanol / 2 h / Ambient temperature

5: Imidazole / dimethylformamide / 3 h / 60 °C

6: 95.3 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

7: pyridine / 0 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; Tattratic acid; tri-n-butyl-tin hydride; (-)-diethyl tartrate; sodium iodide; In pyridine; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; butanone;
DOI:10.1021/jo00188a014

Reference yield:

: 86561-75-3
(E)-5-((2R,3R)-3-(hydroxymethyl)-3-methyloxiran-2-yl)-3-methylpent-2-en-1-yl acetate

: 90461-01-1
Toluene-4-sulfonic acid (S)-2-{(2R,5S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-2-hydroxy-propyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 94.7 percent / Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

2: 94 percent / 5percent HClO₄ / acetonitrile / 4 h / Ambient temperature

3: 90 percent / Phosphorus oxychloride / CH₂Cl₂ / 24 h / Ambient temperature

4: 90 percent / K₂CO₃ / methanol / 1 h / 0 °C

5: 83 percent / Dowex H⁺ / methanol / 24 h / Ambient temperature

6: 60 percent / 1.) Ti(O-i-Pr), (-)-Diethyl D-tatrate, t-BuOOH, 2.) Tattratic acid / CH₂Cl₂ / 1.) -23 degC, 30 min. 2.) stirring

7: 82.5 percent / pyridine / 0 °C / overnight

8: NaI / butan-2-one / 3 h / Heating

9: 98.4 percent / Tri-n-butyltin hydride / ethanol / 2 h / Ambient temperature

10: Imidazole / dimethylformamide / 3 h / 60 °C

11: 95.3 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

12: pyridine / 0 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; perchloric acid; Dowex H⁺; Tattratic acid; tri-n-butyl-tin hydride; potassium carbonate; (-)-diethyl tartrate; triethylamine; sodium iodide; trichlorophosphate; In pyridine; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; butanone;
DOI:10.1021/jo00188a014