Toluene-4-sulfonic acid (2S,3S)-3-hydroxy-2-methoxy-5-phenyl-pentyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2S,3S)-3-hydroxy-2-methoxy-5-phenyl-pentyl ester
CAS No.:88842-06-2
Molecular Formula:C₁₉H₂₄O₅S
Molecular Weight:364.463
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2S,3S)-3-hydroxy-2-methoxy-5-phenyl-pentyl ester

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Chemical Property of Toluene-4-sulfonic acid (2S,3S)-3-hydroxy-2-methoxy-5-phenyl-pentyl ester

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Technology Process of Toluene-4-sulfonic acid (2S,3S)-3-hydroxy-2-methoxy-5-phenyl-pentyl ester

There total 11 articles about Toluene-4-sulfonic acid (2S,3S)-3-hydroxy-2-methoxy-5-phenyl-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: 83.0%

: 88842-05-1
2-Methoxy-5-phenyl-1,3-pentanediol

: 98-59-9
p-toluenesulfonyl chloride

: 88842-06-2
Toluene-4-sulfonic acid (2S,3S)-3-hydroxy-2-methoxy-5-phenyl-pentyl ester

Guidance literature:: With pyridine; at 0 ℃; for 24h;
DOI:10.1021/jo00181a020

Reference yield:

: 75553-23-0
(E)-5-phenyl-2-penten-1-ol

: 88842-06-2
Toluene-4-sulfonic acid (2S,3S)-3-hydroxy-2-methoxy-5-phenyl-pentyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 287 mg / p-TsOH / tetrahydrofuran / 4 h / Ambient temperature

2: 322 mg / tetrabutylammonium hydroxide, t-BuOOH, OsO₄ / 2-methyl-propan-2-ol / 18 h / 0 °C

3: 95 mg / NaH / tetrahydrofuran / 2 h / Ambient temperature

4: 66 mg / 1N HCl / 14 h / Ambient temperature

5: 83 percent / pyridine / 24 h / 0 °C

With pyridine; hydrogenchloride; tert.-butylhydroperoxide; osmium(VIII) oxide; tetra(n-butyl)ammonium hydroxide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; tert-butyl alcohol;
DOI:10.1021/jo00181a020

Reference yield:

: 39520-63-3,75553-23-0,106262-48-0
(Z)-5-phenylpent-2-en-1-ol

: 88842-06-2
Toluene-4-sulfonic acid (2S,3R)-3-hydroxy-2-methoxy-5-phenyl-pentyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: p-TsOH / tetrahydrofuran / Ambient temperature

2: tetrabutylammonium hydroxide, t-BuOOH, OsO₄ / 2-methyl-propan-2-ol / 0 °C

3: NaH / tetrahydrofuran / Ambient temperature

4: 1N HCl / Ambient temperature

5: pyridine / 0 °C

With pyridine; hydrogenchloride; tert.-butylhydroperoxide; osmium(VIII) oxide; tetra(n-butyl)ammonium hydroxide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; tert-butyl alcohol;
DOI:10.1021/jo00181a020