Benzoic acid (2Z,5Z)-(R)-9-methoxycarbonyl-1-[(2R,3S)-((Z)-3-oct-2-enyl)-oxiranyl]-nona-2,5-dienyl ester

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Chemical Name:Benzoic acid (2Z,5Z)-(R)-9-methoxycarbonyl-1-[(2R,3S)-((Z)-3-oct-2-enyl)-oxiranyl]-nona-2,5-dienyl ester
CAS No.:160017-33-4
Molecular Formula:C₂₈H₃₈O₅
Molecular Weight:454.607
Hs Code.:

Synonyms:Benzoic acid (2Z,5Z)-(R)-9-methoxycarbonyl-1-[(2R,3S)-((Z)-3-oct-2-enyl)-oxiranyl]-nona-2,5-dienyl ester

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Chemical Property of Benzoic acid (2Z,5Z)-(R)-9-methoxycarbonyl-1-[(2R,3S)-((Z)-3-oct-2-enyl)-oxiranyl]-nona-2,5-dienyl ester

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Technology Process of Benzoic acid (2Z,5Z)-(R)-9-methoxycarbonyl-1-[(2R,3S)-((Z)-3-oct-2-enyl)-oxiranyl]-nona-2,5-dienyl ester

There total 12 articles about Benzoic acid (2Z,5Z)-(R)-9-methoxycarbonyl-1-[(2R,3S)-((Z)-3-oct-2-enyl)-oxiranyl]-nona-2,5-dienyl 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: 80.0%

: 89408-74-2
Methyl (10S,11R,12S)-10-hydroxy-11,12,-epoxyeicosa-5(Z),8(Z),14(Z)-trienoate

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

: 160017-33-4
Benzoic acid (2Z,5Z)-(R)-9-methoxycarbonyl-1-[(2R,3S)-((Z)-3-oct-2-enyl)-oxiranyl]-nona-2,5-dienyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In benzene; at 23 ℃; for 2h;
DOI:10.1016/S0040-4039(00)73491-5

Reference yield:

: 16666-79-8,19493-12-0
hexylidenetriphenylphosphoran

: 160017-33-4
Benzoic acid (2Z,5Z)-(R)-9-methoxycarbonyl-1-[(2R,3S)-((Z)-3-oct-2-enyl)-oxiranyl]-nona-2,5-dienyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: tetrahydrofuran / - 78 deg C, 0.5 h, 23 deg C, 12 h

2: 1.) (COCl)2/DMSO; 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C, 1 h; 2.) -78 to 23 deg C, 0.3 h

3: tetrahydrofuran; toluene / -78 deg C, 0.1 h; -40 deg C, 1 h; 0 deg C, 0.5 h

4: 99 percent / 0.5percent HCl / methanol / 12 h / 23 °C

5: 87 percent / DMAP/Et₃N / CH₂Cl₂ / 48 h / -28 °C

6: 78 percent / NaOMe / methanol / 3 h / 0 °C

7: 82 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 23 °C

8: 80 percent / DEAD/Ph₃P / benzene / 2 h / 23 °C

With hydrogenchloride; dmap; oxalyl dichloride; sodium methylate; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; benzene;
DOI:10.1016/S0040-4039(00)73491-5

Reference yield:

: 160080-76-2
(3aR,7S,7aS)-7-Hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

: 160017-33-4
Benzoic acid (2Z,5Z)-(R)-9-methoxycarbonyl-1-[(2R,3S)-((Z)-3-oct-2-enyl)-oxiranyl]-nona-2,5-dienyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 95 percent / Ph₃CBF₄ / diethyl ether / 1 h / 0 °C

2: 1.) OsO₄, NMO; 2.) Pb(OAc)4, Na₂CO₃; 3.) LiAlH₄ / 1.) acetone/water, 23 deg C, 4 h; 2.) CH₂Cl₂, -78 deg C, 0.25 h; 3.) THF, 23 deg C, 3 h

3: Pb(OAc)4, Na₂CO₃ / CH₂Cl₂ / 0.25 h / -78 °C

4: tetrahydrofuran / - 78 deg C, 0.5 h, 23 deg C, 12 h

5: 1.) (COCl)2/DMSO; 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C, 1 h; 2.) -78 to 23 deg C, 0.3 h

6: tetrahydrofuran; toluene / -78 deg C, 0.1 h; -40 deg C, 1 h; 0 deg C, 0.5 h

7: 99 percent / 0.5percent HCl / methanol / 12 h / 23 °C

8: 87 percent / DMAP/Et₃N / CH₂Cl₂ / 48 h / -28 °C

9: 78 percent / NaOMe / methanol / 3 h / 0 °C

10: 82 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 23 °C

11: 80 percent / DEAD/Ph₃P / benzene / 2 h / 23 °C

With lead(IV) acetate; hydrogenchloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; oxalyl dichloride; sodium methylate; trityl tetrafluoroborate; sodium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; benzene;
DOI:10.1016/S0040-4039(00)73491-5