Acetic acid (1R,2S)-1-isopropyl-2-methyl-3-(toluene-4-sulfonyloxy)-propyl ester

Base Information

Chemical Name:Acetic acid (1R,2S)-1-isopropyl-2-methyl-3-(toluene-4-sulfonyloxy)-propyl ester
CAS No.:179815-35-1
Molecular Formula:C₁₆H₂₄O₅S
Molecular Weight:328.43
Hs Code.:

Synonyms:Acetic acid (1R,2S)-1-isopropyl-2-methyl-3-(toluene-4-sulfonyloxy)-propyl ester

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Chemical Property of Acetic acid (1R,2S)-1-isopropyl-2-methyl-3-(toluene-4-sulfonyloxy)-propyl ester

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Technology Process of Acetic acid (1R,2S)-1-isopropyl-2-methyl-3-(toluene-4-sulfonyloxy)-propyl ester

There total 5 articles about Acetic acid (1R,2S)-1-isopropyl-2-methyl-3-(toluene-4-sulfonyloxy)-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: 92.0%

: 108-24-7
acetic anhydride

: 171234-19-8
(2S,3R) 2,4-dimethyl-1-<(p-toluenesulfonyl)oxy>pentan-3-ol

: 179815-35-1
Acetic acid (1R,2S)-1-isopropyl-2-methyl-3-(toluene-4-sulfonyloxy)-propyl ester

Guidance literature:: With dmap; triethylamine; for 8h; Ambient temperature;
DOI:10.1021/ja961071u

Reference yield:

: 15790-86-0
ethyl-4-methyl-2-(E)-penteneoate

: 179815-35-1
Acetic acid (1R,2S)-1-isopropyl-2-methyl-3-(toluene-4-sulfonyloxy)-propyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / iBu₂AlH / tetrahydrofuran / -78 - 0 °C

2: 74 percent / (-)-diethyl tartrate, Ti(i-Pr)4, t-BuOOH / CH₂Cl₂ / 20 h / -20 °C

3: 2.) NaIO₄ / 1.) Et₂O, 0 deg C, 3.5 h, 2.) H₂O, 16 h

4: 82 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

5: 92 percent / Et₃N, 4-(dimethylamino)pyridine / 8 h / Ambient temperature

With pyridine; tert.-butylhydroperoxide; dmap; sodium periodate; diisobutylaluminium hydride; isopropyl titanoate(IV); (-)-diethyl tartrate; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja961071u

Reference yield:

: 69143-05-1
(E)-4-methyl-pent-2-en-1-ol

: 179815-35-1
Acetic acid (1R,2S)-1-isopropyl-2-methyl-3-(toluene-4-sulfonyloxy)-propyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 74 percent / (-)-diethyl tartrate, Ti(i-Pr)4, t-BuOOH / CH₂Cl₂ / 20 h / -20 °C

2: 2.) NaIO₄ / 1.) Et₂O, 0 deg C, 3.5 h, 2.) H₂O, 16 h

3: 82 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

4: 92 percent / Et₃N, 4-(dimethylamino)pyridine / 8 h / Ambient temperature

With pyridine; tert.-butylhydroperoxide; dmap; sodium periodate; isopropyl titanoate(IV); (-)-diethyl tartrate; triethylamine; In dichloromethane;
DOI:10.1021/ja961071u