Toluene-4-sulfonic acid (S)-2-hydroxy-2-[(2R,4R,5R,6S)-4-hydroxy-5-methyl-6-((E)-styryl)-tetrahydro-pyran-2-yl]-ethyl ester

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Chemical Name:Toluene-4-sulfonic acid (S)-2-hydroxy-2-[(2R,4R,5R,6S)-4-hydroxy-5-methyl-6-((E)-styryl)-tetrahydro-pyran-2-yl]-ethyl ester
CAS No.:913066-79-2
Molecular Formula:C₂₃H₂₈O₆S
Molecular Weight:432.538
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (S)-2-hydroxy-2-[(2R,4R,5R,6S)-4-hydroxy-5-methyl-6-((E)-styryl)-tetrahydro-pyran-2-yl]-ethyl ester

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Chemical Property of Toluene-4-sulfonic acid (S)-2-hydroxy-2-[(2R,4R,5R,6S)-4-hydroxy-5-methyl-6-((E)-styryl)-tetrahydro-pyran-2-yl]-ethyl ester

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Technology Process of Toluene-4-sulfonic acid (S)-2-hydroxy-2-[(2R,4R,5R,6S)-4-hydroxy-5-methyl-6-((E)-styryl)-tetrahydro-pyran-2-yl]-ethyl ester

There total 10 articles about Toluene-4-sulfonic acid (S)-2-hydroxy-2-[(2R,4R,5R,6S)-4-hydroxy-5-methyl-6-((E)-styryl)-tetrahydro-pyran-2-yl]-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: 75.0%

: Toluene-4-sulfonic acid (2S,3S)-3-[(4R,5R,6S)-2-(4-methoxy-phenyl)-5-methyl-6-((E)-styryl)-[1,3]dioxan-4-ylmethyl]-oxiranylmethyl ester

: 913066-79-2
Toluene-4-sulfonic acid (S)-2-hydroxy-2-[(2R,4R,5R,6S)-4-hydroxy-5-methyl-6-((E)-styryl)-tetrahydro-pyran-2-yl]-ethyl ester

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; methanol; at 25 ℃; for 14h;
DOI:10.1021/ol061339e

Reference yield:

: 913066-83-8
(E)-(2S,3S)-2-Methyl-5-phenyl-3-trimethylsilanyloxy-pent-4-enal

: 913066-79-2
Toluene-4-sulfonic acid (S)-2-hydroxy-2-[(2R,4R,5R,6S)-4-hydroxy-5-methyl-6-((E)-styryl)-tetrahydro-pyran-2-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: diethyl ether / 0.25 h / -78 °C

2: aq. HCl / tetrahydrofuran / 1 h

3: 94 percent / pyridinium p-toluenesulfonate / benzene / 1.5 h / 25 °C

4: 95 percent / Cl₂(PCy₃)(IMes)Ru=CHPh / CH₂Cl₂ / 14 h / 20 °C

5: 93 percent / i-Bu₂AlH / CH₂Cl₂; hexane / 0.25 h / -78 °C

6: 68 percent / Ti(i-PrO)4; (+)-diethyl tartrate; t-BuOOH / CH₂Cl₂ / 14 h / cooling

7: 81 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 0 °C

8: 75 percent / aq. HCl / tetrahydrofuran; methanol / 14 h / 25 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; (+)-Weinsaeure-diethylester; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/ol061339e

Reference yield:

: 913066-84-9
(E)-(3S,4R,5R)-4-Methyl-1-phenyl-octa-1,7-diene-3,5-diol

: 913066-79-2
Toluene-4-sulfonic acid (S)-2-hydroxy-2-[(2R,4R,5R,6S)-4-hydroxy-5-methyl-6-((E)-styryl)-tetrahydro-pyran-2-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / pyridinium p-toluenesulfonate / benzene / 1.5 h / 25 °C

2: 95 percent / Cl₂(PCy₃)(IMes)Ru=CHPh / CH₂Cl₂ / 14 h / 20 °C

3: 93 percent / i-Bu₂AlH / CH₂Cl₂; hexane / 0.25 h / -78 °C

4: 68 percent / Ti(i-PrO)4; (+)-diethyl tartrate; t-BuOOH / CH₂Cl₂ / 14 h / cooling

5: 81 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 0 °C

6: 75 percent / aq. HCl / tetrahydrofuran; methanol / 14 h / 25 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; (+)-Weinsaeure-diethylester; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
DOI:10.1021/ol061339e