Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2S,5R)-2-methyl-5-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2S,5R)-2-methyl-5-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester
CAS No.:90481-26-8
Molecular Formula:C₁₈H₂₄O₈S
Molecular Weight:400.45
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2S,5R)-2-methyl-5-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

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Chemical Property of Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2S,5R)-2-methyl-5-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

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Technology Process of Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2S,5R)-2-methyl-5-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

There total 8 articles about Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2S,5R)-2-methyl-5-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-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: 82.5%

: 90481-25-7
(S)-4-[(2R,5S)-5-((R)-1,2-Dihydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-4-methyl-[1,3]dioxolan-2-one

: 98-59-9
p-toluenesulfonyl chloride

: 90481-26-8
Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2S,5R)-2-methyl-5-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

Guidance literature:: In pyridine; at 0 ℃; overnight;
DOI:10.1021/jo00188a014

Reference yield:

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

: 90481-26-8
Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2S,5R)-2-methyl-5-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 8 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; perchloric acid; diethyl (2S,3S)-tartrate; Dowex H⁺; Tattratic acid; potassium carbonate; (-)-diethyl tartrate; triethylamine; trichlorophosphate; In pyridine; methanol; dichloromethane; acetonitrile;
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

: 90481-26-8
Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2S,5R)-2-methyl-5-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 2 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; Tattratic acid; (-)-diethyl tartrate; In pyridine; dichloromethane;
DOI:10.1021/jo00188a014