(2R,7S,8S)-7-chloro-3,6,7,8-tetrahydro-2-(3-hydroxypropyl)-8-<<(p-tolylsulfonyl)oxy>methyl>-4-(trimethylsilyl)-2H-oxocin

Base Information

Chemical Name:(2R,7S,8S)-7-chloro-3,6,7,8-tetrahydro-2-(3-hydroxypropyl)-8-<<(p-tolylsulfonyl)oxy>methyl>-4-(trimethylsilyl)-2H-oxocin
CAS No.:112793-75-6
Molecular Formula:C₂₁H₃₃ClO₅SSi
Molecular Weight:461.095
Hs Code.:

Synonyms:(2R,7S,8S)-7-chloro-3,6,7,8-tetrahydro-2-(3-hydroxypropyl)-8-<<(p-tolylsulfonyl)oxy>methyl>-4-(trimethylsilyl)-2H-oxocin

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Chemical Property of (2R,7S,8S)-7-chloro-3,6,7,8-tetrahydro-2-(3-hydroxypropyl)-8-<<(p-tolylsulfonyl)oxy>methyl>-4-(trimethylsilyl)-2H-oxocin

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Technology Process of (2R,7S,8S)-7-chloro-3,6,7,8-tetrahydro-2-(3-hydroxypropyl)-8-<<(p-tolylsulfonyl)oxy>methyl>-4-(trimethylsilyl)-2H-oxocin

There total 9 articles about (2R,7S,8S)-7-chloro-3,6,7,8-tetrahydro-2-(3-hydroxypropyl)-8-<<(p-tolylsulfonyl)oxy>methyl>-4-(trimethylsilyl)-2H-oxocin 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:

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

: 112793-75-6
(2R,7S,8S)-7-chloro-3,6,7,8-tetrahydro-2-(3-hydroxypropyl)-8-<<(p-tolylsulfonyl)oxy>methyl>-4-(trimethylsilyl)-2H-oxocin

Guidance literature:: Multi-step reaction with 10 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

8: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h / 23 °C

9: SnCl₄ / CH₂Cl₂ / 1.5 h / 0 °C

10: n-Bu₄NF / tetrahydrofuran / 2 h

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; diethyl (2R,3R)-tartrate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sec.-butyllithium; sodium acetate; pyridinium p-toluenesulfonate; tin(IV) chloride; 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

: 112793-75-6
(2R,7S,8S)-7-chloro-3,6,7,8-tetrahydro-2-(3-hydroxypropyl)-8-<<(p-tolylsulfonyl)oxy>methyl>-4-(trimethylsilyl)-2H-oxocin

Guidance literature:: Multi-step reaction with 8 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

6: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h / 23 °C

7: SnCl₄ / CH₂Cl₂ / 1.5 h / 0 °C

8: n-Bu₄NF / tetrahydrofuran / 2 h

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

Reference yield:

: 112793-67-6
4-Trimethylsilanyl-pent-4-en-1-ol

: 112793-75-6
(2R,7S,8S)-7-chloro-3,6,7,8-tetrahydro-2-(3-hydroxypropyl)-8-<<(p-tolylsulfonyl)oxy>methyl>-4-(trimethylsilyl)-2H-oxocin

Guidance literature:: Multi-step reaction with 9 steps

1: 89 percent / pyridinium chlorochromate, NaOAc / CH₂Cl₂ / 2 h

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

3: 93 percent / diisobutylaluminium hydride / hexane; CH₂Cl₂ / 1 h / -70 to -20 deg C

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

5: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH₂Cl₂ / 15 h / 23 °C

6: 88 percent / pyridine / 48 h / 23 °C

7: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h / 23 °C

8: SnCl₄ / CH₂Cl₂ / 1.5 h / 0 °C

9: n-Bu₄NF / tetrahydrofuran / 2 h

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium acetate; pyridinium p-toluenesulfonate; tin(IV) chloride; trimethylamine hydrochloride; potassium hexamethylsilazane; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; 2,2,4-trimethylpentane; hexane; dichloromethane; toluene;
DOI:10.1021/ja00215a040