Benzoic acid (E)-(1S,4S)-4-methyl-1-((S)-1-methyl-prop-2-ynyl)-5-(tetrahydro-pyran-2-yloxy)-pent-2-enyl ester

Base Information

Chemical Name:Benzoic acid (E)-(1S,4S)-4-methyl-1-((S)-1-methyl-prop-2-ynyl)-5-(tetrahydro-pyran-2-yloxy)-pent-2-enyl ester
CAS No.:853211-61-7
Molecular Formula:C₂₂H₂₈O₄
Molecular Weight:356.462
Hs Code.:

Synonyms:Benzoic acid (E)-(1S,4S)-4-methyl-1-((S)-1-methyl-prop-2-ynyl)-5-(tetrahydro-pyran-2-yloxy)-pent-2-enyl ester

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Chemical Property of Benzoic acid (E)-(1S,4S)-4-methyl-1-((S)-1-methyl-prop-2-ynyl)-5-(tetrahydro-pyran-2-yloxy)-pent-2-enyl ester

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Technology Process of Benzoic acid (E)-(1S,4S)-4-methyl-1-((S)-1-methyl-prop-2-ynyl)-5-(tetrahydro-pyran-2-yloxy)-pent-2-enyl ester

There total 9 articles about Benzoic acid (E)-(1S,4S)-4-methyl-1-((S)-1-methyl-prop-2-ynyl)-5-(tetrahydro-pyran-2-yloxy)-pent-2-enyl ester 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: 40.0%

: 853211-36-6
(E)-(3S,4R,7S)-3,7-Dimethyl-8-(tetrahydro-pyran-2-yloxy)-oct-5-en-1-yn-4-ol

: 65-85-0,8013-63-6
benzoic acid

: 853211-61-7
Benzoic acid (E)-(1S,4S)-4-methyl-1-((S)-1-methyl-prop-2-ynyl)-5-(tetrahydro-pyran-2-yloxy)-pent-2-enyl ester

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at -78 ℃; for 0.166667h;
DOI:10.1055/s-2005-864804

Reference yield:

: 853211-34-4
Diisopropyl-carbamic acid (1Z,5E)-(3S,4R,7S)-4-hydroxy-3,7-dimethyl-8-(tetrahydro-pyran-2-yloxy)-octa-1,5-dienyl ester

: 853211-61-7
Benzoic acid (E)-(1S,4S)-4-methyl-1-((S)-1-methyl-prop-2-ynyl)-5-(tetrahydro-pyran-2-yloxy)-pent-2-enyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / t-BuLi / diethyl ether / 0.75 h / -78 °C

2: 40 percent / DIAD; PPh₃ / toluene / 0.17 h / -78 °C

With di-isopropyl azodicarboxylate; tert.-butyl lithium; triphenylphosphine; In diethyl ether; toluene;
DOI:10.1055/s-2005-864804

Reference yield:

: 110-87-2
3,4-dihydro-2H-pyran

: 853211-61-7
Benzoic acid (E)-(1S,4S)-4-methyl-1-((S)-1-methyl-prop-2-ynyl)-5-(tetrahydro-pyran-2-yloxy)-pent-2-enyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 95 percent / ATPS / 12 h / 20 °C

2.1: 85 percent / LAH / tetrahydrofuran / 3 h / 0 °C

3.1: 100 percent / IBX / dimethylsulfoxide / 2 h / 20 °C

4.1: 81 percent / toluene / 10 h / 50 °C

5.1: 80 percent / DIBALH / tetrahydrofuran / 1 h / -78 °C

6.1: 95 percent / IBX / dimethylsulfoxide / 2 h / 20 °C

7.1: n-BuLi; (-)-sparteine / hexane / 3.17 h / -78 °C

7.2: Ti(O-i-Pr)4 / hexane; pentane / 0.5 h / -78 °C

7.3: 85 percent / hexane; pentane / 2 h / -78 °C

8.1: 70 percent / t-BuLi / diethyl ether / 0.75 h / -78 °C

9.1: 40 percent / DIAD; PPh₃ / toluene / 0.17 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; adenosine-5'-O-(3-thiotriphosphate); di-isopropyl azodicarboxylate; tert.-butyl lithium; diisobutylaluminium hydride; triphenylphosphine; (-)-sparteine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; hexane; dimethyl sulfoxide; toluene; 7.3: Hoppe crotylation;
DOI:10.1055/s-2005-864804