(2E)-5-[(1'S,2'R,4'S)-4'-p-nitrobenzoxy-1',2'-epoxy-2',6',6'-trimethylcyclohex-1'-yl]-4-acetoxy-3-methylpenta-2-en-1-ol

Base Information

Chemical Name:(2E)-5-[(1'S,2'R,4'S)-4'-p-nitrobenzoxy-1',2'-epoxy-2',6',6'-trimethylcyclohex-1'-yl]-4-acetoxy-3-methylpenta-2-en-1-ol
CAS No.:1354744-33-4
Molecular Formula:C₂₄H₃₁NO₈
Molecular Weight:461.512
Hs Code.:

Synonyms:(2E)-5-[(1'S,2'R,4'S)-4'-p-nitrobenzoxy-1',2'-epoxy-2',6',6'-trimethylcyclohex-1'-yl]-4-acetoxy-3-methylpenta-2-en-1-ol

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Chemical Property of (2E)-5-[(1'S,2'R,4'S)-4'-p-nitrobenzoxy-1',2'-epoxy-2',6',6'-trimethylcyclohex-1'-yl]-4-acetoxy-3-methylpenta-2-en-1-ol

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Technology Process of (2E)-5-[(1'S,2'R,4'S)-4'-p-nitrobenzoxy-1',2'-epoxy-2',6',6'-trimethylcyclohex-1'-yl]-4-acetoxy-3-methylpenta-2-en-1-ol

There total 6 articles about (2E)-5-[(1'S,2'R,4'S)-4'-p-nitrobenzoxy-1',2'-epoxy-2',6',6'-trimethylcyclohex-1'-yl]-4-acetoxy-3-methylpenta-2-en-1-ol 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: 81.0%

: 1354744-23-2
(2E)-tert-butyldimethyl{5-[(1'S,2'R,4'S)-4'-p-nitrobenzoxy-1',2'-epoxy-2',6',6'-trimethylcyclohex-1'-yl]-4-acetoxy-3-methylpent-2-enyloxy}silane

: 1354744-33-4
(2E)-5-[(1'S,2'R,4'S)-4'-p-nitrobenzoxy-1',2'-epoxy-2',6',6'-trimethylcyclohex-1'-yl]-4-acetoxy-3-methylpenta-2-en-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.333333h;
DOI:10.1021/ol203344c

Reference yield:

: 1354744-21-0
C₁₇H₃₂O₂Si

: 1354744-33-4
(2E)-5-[(1'S,2'R,4'S)-4'-p-nitrobenzoxy-1',2'-epoxy-2',6',6'-trimethylcyclohex-1'-yl]-4-acetoxy-3-methylpenta-2-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: tert.-butyl lithium / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

1.2: 0.33 h / -78 °C

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

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

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

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

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

With pyridine; methanol; tert.-butylhydroperoxide; dmap; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; aluminum tri-tert-butoxide; triphenylphosphine; In tetrahydrofuran; pyridine; diethyl ether; toluene; 5.1: Mitsunobu reaction;
DOI:10.1021/ol203344c

Reference yield:

: 1354744-22-1
(2E)-tert-butyldimethyl{5-[(4'S)-4'-hydroxy-2',6',6'-trimethylcyclohexenyl]-4-acetoxy-3-methylpent-2-enyloxy}silane

: 1354744-33-4
(2E)-5-[(1'S,2'R,4'S)-4'-p-nitrobenzoxy-1',2'-epoxy-2',6',6'-trimethylcyclohex-1'-yl]-4-acetoxy-3-methylpenta-2-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

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

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

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

With tert.-butylhydroperoxide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; aluminum tri-tert-butoxide; triphenylphosphine; In tetrahydrofuran; toluene; 2: Mitsunobu reaction;
DOI:10.1021/ol203344c