(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

Base Information

Chemical Name:(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
CAS No.:1354744-23-2
Molecular Formula:C₃₀H₄₅NO₈Si
Molecular Weight:575.775
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 6 articles about (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 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: 70.0%

: 1354744-32-3
(2E)-tert-butyldimethyl{5-[(1'S,2'R,4'R)-4'-hydroxy-1',2'-epoxy-2',6',6'-trimethylcyclohex-1'-yl]-4-acetoxy-3-methylpent-2-enyloxy}silane

: 62-23-7
4-nitro-benzoic acid

: 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

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 1h;
DOI:10.1021/ol203344c

Reference yield:

: 1354744-21-0
C₁₇H₃₂O₂Si

: 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

Guidance literature:: Multi-step reaction with 5 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

With pyridine; methanol; tert.-butylhydroperoxide; dmap; di-isopropyl azodicarboxylate; 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:

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

: 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

Guidance literature:: Multi-step reaction with 3 steps

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

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

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

With methanol; tert.-butylhydroperoxide; di-isopropyl azodicarboxylate; pyridinium p-toluenesulfonate; aluminum tri-tert-butoxide; triphenylphosphine; In tetrahydrofuran; toluene; 3: Mitsunobu reaction;
DOI:10.1021/ol203344c