<(2S,3S)-3-chloro-2-hydroxy-6-(trimethylsilyl)-6-heptenyl> 1-p-toluenesulfonate

Base Information

Chemical Name:<(2S,3S)-3-chloro-2-hydroxy-6-(trimethylsilyl)-6-heptenyl> 1-p-toluenesulfonate
CAS No.:112793-73-4
Molecular Formula:C₁₇H₂₇ClO₄SSi
Molecular Weight:391.003
Hs Code.:

Synonyms:<(2S,3S)-3-chloro-2-hydroxy-6-(trimethylsilyl)-6-heptenyl> 1-p-toluenesulfonate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of <(2S,3S)-3-chloro-2-hydroxy-6-(trimethylsilyl)-6-heptenyl> 1-p-toluenesulfonate

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Technology Process of <(2S,3S)-3-chloro-2-hydroxy-6-(trimethylsilyl)-6-heptenyl> 1-p-toluenesulfonate

There total 7 articles about <(2S,3S)-3-chloro-2-hydroxy-6-(trimethylsilyl)-6-heptenyl> 1-p-toluenesulfonate 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: 88.0%

: 112817-44-4
(2S,3S)-3-chloro-2-hydroxy-6-(trimethylsilyl)-6-hepten-1-ol

: 98-59-9
p-toluenesulfonyl chloride

: 112793-73-4
<(2S,3S)-3-chloro-2-hydroxy-6-(trimethylsilyl)-6-heptenyl> 1-p-toluenesulfonate

Guidance literature:: With pyridine; at 23 ℃; for 48h;
DOI:10.1021/ja00215a040

Reference yield:

: 13683-41-5
1-bromo-1-(trimethylsilyl)ethene

: 112793-73-4
<(2S,3S)-3-chloro-2-hydroxy-6-(trimethylsilyl)-6-heptenyl> 1-p-toluenesulfonate

Guidance literature:: Multi-step reaction with 7 steps

1: 77 percent / sec-BuLi, BF₃*OEt₂ / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C

2: 89 percent / pyridinium chlorochromate, NaOAc / CH₂Cl₂ / 2 h

3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C

4: 93 percent / diisobutylaluminium hydride / hexane; CH₂Cl₂ / 1 h / -70 to -20 deg C

5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 15 h / 4 °C

6: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH₂Cl₂ / 15 h / 23 °C

7: 88 percent / pyridine / 48 h / 23 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; diethyl (2R,3R)-tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; sec.-butyllithium; sodium acetate; trimethylamine hydrochloride; potassium hexamethylsilazane; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; cyclohexane; toluene;
DOI:10.1021/ja00215a040

Reference yield:

: 112793-68-7
4-(trimethylsilyl)-4-pentenal

: 112793-73-4
<(2S,3S)-3-chloro-2-hydroxy-6-(trimethylsilyl)-6-heptenyl> 1-p-toluenesulfonate

Guidance literature:: Multi-step reaction with 5 steps

1: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C

2: 93 percent / diisobutylaluminium hydride / hexane; CH₂Cl₂ / 1 h / -70 to -20 deg C

3: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 15 h / 4 °C

4: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH₂Cl₂ / 15 h / 23 °C

5: 88 percent / pyridine / 48 h / 23 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; diethyl (2R,3R)-tartrate; 4 A molecular sieve; trimethylamine hydrochloride; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; 2,2,4-trimethylpentane; hexane; dichloromethane; toluene;
DOI:10.1021/ja00215a040