(2E)-tert-butyldimethyl{5-[(4'S)-4'-triethylsilyloxy-2',6',6'-trimethylcyclohexenyl]-4-hydroxy-3-methylpent-2-enyloxy}silane

Base Information

Chemical Name:(2E)-tert-butyldimethyl{5-[(4'S)-4'-triethylsilyloxy-2',6',6'-trimethylcyclohexenyl]-4-hydroxy-3-methylpent-2-enyloxy}silane
CAS No.:1354744-19-6
Molecular Formula:C₂₇H₅₄O₃Si₂
Molecular Weight:482.895
Hs Code.:

Synonyms:(2E)-tert-butyldimethyl{5-[(4'S)-4'-triethylsilyloxy-2',6',6'-trimethylcyclohexenyl]-4-hydroxy-3-methylpent-2-enyloxy}silane

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Chemical Property of (2E)-tert-butyldimethyl{5-[(4'S)-4'-triethylsilyloxy-2',6',6'-trimethylcyclohexenyl]-4-hydroxy-3-methylpent-2-enyloxy}silane

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Technology Process of (2E)-tert-butyldimethyl{5-[(4'S)-4'-triethylsilyloxy-2',6',6'-trimethylcyclohexenyl]-4-hydroxy-3-methylpent-2-enyloxy}silane

There total 1 articles about (2E)-tert-butyldimethyl{5-[(4'S)-4'-triethylsilyloxy-2',6',6'-trimethylcyclohexenyl]-4-hydroxy-3-methylpent-2-enyloxy}silane 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: 90.0%

: 1354744-21-0
C₁₇H₃₂O₂Si

: 152893-54-4
(E)-tert-butyl((3-iodobut-2-en-1-yl)oxy)dimethylsilane

: 1354744-19-6
(2E)-tert-butyldimethyl{5-[(4'S)-4'-triethylsilyloxy-2',6',6'-trimethylcyclohexenyl]-4-hydroxy-3-methylpent-2-enyloxy}silane

Guidance literature:: (E)-tert-butyl((3-iodobut-2-en-1-yl)oxy)dimethylsilane; With tert.-butyl lithium; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.5h;

C₁₇H₃₂O₂Si; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.333333h;
DOI:10.1021/ol203344c

Reference yield: 93.0%

: 1354744-19-6
(2E)-tert-butyldimethyl{5-[(4'S)-4'-triethylsilyloxy-2',6',6'-trimethylcyclohexenyl]-4-hydroxy-3-methylpent-2-enyloxy}silane

: 108-24-7
acetic anhydride

: 1354744-20-9
(2E)-tert-butyldimethyl{5-[(4'S)-4'-triethylsilyloxy-2',6',6'-trimethylcyclohexenyl]-4-acetoxy-3-methylpent-2-enyloxy}silane

Guidance literature:: With pyridine; dmap; In pyridine; at 20 ℃; for 0.5h;
DOI:10.1021/ol203344c

Reference yield:

: 1354744-19-6
(2E)-tert-butyldimethyl{5-[(4'S)-4'-triethylsilyloxy-2',6',6'-trimethylcyclohexenyl]-4-hydroxy-3-methylpent-2-enyloxy}silane

: C₄₈H₇₄O₆Si

Guidance literature:: Multi-step reaction with 16 steps

1.1: pyridine; dmap / pyridine / 0.5 h / 20 °C

2.1: methanol; pyridinium p-toluenesulfonate / 0.17 h / 20 °C

3.1: tert.-butylhydroperoxide; aluminum tri-tert-butoxide / toluene / 2 h / 0 - 20 °C

4.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / 0 - 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C

6.1: manganese(IV) oxide / tetrahydrofuran / 0.42 h / 20 °C

7.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium / tetrahydrofuran / 0.33 h / 0 °C

7.2: 0.08 h / -78 - 20 °C

8.1: potassium hydroxide / methanol; water / 0.08 h / 20 °C

9.1: 1H-imidazole / N,N-dimethyl-formamide / 0.17 h / 20 °C

10.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.17 h / -78 °C

11.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.33 h / 0 - 20 °C

12.1: Dess-Martin periodane / dichloromethane / 0.17 h / 20 °C

13.1: hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide / ethanol; water / 0.83 h / 0 - 20 °C

14.1: 1H-imidazole / N,N-dimethyl-formamide / 0.17 h / 20 °C

15.1: lithium borohydride / tetrahydrofuran / 0.83 h / 20 °C

16.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.08 h / 0 °C / Darkness

With pyridine; 1H-imidazole; methanol; tert.-butylhydroperoxide; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; manganese(IV) oxide; lithium borohydride; n-butyllithium; hexaammonium heptamolybdate tetrahydrate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; aluminum tri-tert-butoxide; Dess-Martin periodane; triphenylphosphine; potassium hydroxide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 4.1: Mitsunobu reaction / 7.1: Horner-Emmons reaction / 11.1: Mitsunobu reaction / 15.1: Luche reduction;
DOI:10.1021/ol203344c