2,4-Dinitro-benzoic acid (E)-(1S,2R)-1-((E)-3-tert-butoxycarbonyl-allyl)-2-methyl-4-phenyl-but-3-enyl ester

Base Information

• Chemical Name: 2,4-Dinitro-benzoic acid (E)-(1S,2R)-1-((E)-3-tert-butoxycarbonyl-allyl)-2-methyl-4-phenyl-but-3-enyl ester
• CAS No.: 182486-11-9
• Molecular Formula: C₂₆H₂₈N₂O₈
• Molecular Weight: 496.517

Synonyms:2,4-Dinitro-benzoic acid (E)-(1S,2R)-1-((E)-3-tert-butoxycarbonyl-allyl)-2-methyl-4-phenyl-but-3-enyl ester

Chemical Property of 2,4-Dinitro-benzoic acid (E)-(1S,2R)-1-((E)-3-tert-butoxycarbonyl-allyl)-2-methyl-4-phenyl-but-3-enyl ester

Chemical Property:

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Technology Process of 2,4-Dinitro-benzoic acid (E)-(1S,2R)-1-((E)-3-tert-butoxycarbonyl-allyl)-2-methyl-4-phenyl-but-3-enyl ester

There total 7 articles about 2,4-Dinitro-benzoic acid (E)-(1S,2R)-1-((E)-3-tert-butoxycarbonyl-allyl)-2-methyl-4-phenyl-but-3-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: 15.0%

2,4-dinitrobenzoic acid (610-30-0) + (2E,7E)-(5R,6R)-5-Hydroxy-6-methyl-8-phenyl-octa-2,7-dienoic acid tert-butyl ester (182486-31-3) → 2,4-Dinitro-benzoic acid (E)-(1S,2R)-1-((E)-3-tert-butoxycarbonyl-allyl)-2-methyl-4-phenyl-but-3-enyl ester (182486-11-9) + (2E,4E,7E)-(S)-6-Methyl-8-phenyl-octa-2,4,7-trienoic acid tert-butyl ester

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 40 ℃; for 50h;

DOI:10.1021/jo960972i

Reference yield:

(E)-methyl 4-phenylbut-3-enoate (91083-82-8,24891-74-5,34541-74-7) → 2,4-Dinitro-benzoic acid (E)-(1S,2R)-1-((E)-3-tert-butoxycarbonyl-allyl)-2-methyl-4-phenyl-but-3-enyl ester (182486-11-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) lithium diisopropylamide / 1.) THF, hexanes, -60 deg C, 10 min, 2.) THF, hexanes, 5 deg C, 15 min

2: phosphate buffer, sodium azide / H₂O / 120 h / 25 °C / 2-propanol-treated Candida rugosa lipase presence, pH 7.0

3: 95 percent / diisobutylaluminum hydride / diethyl ether; hexane / 3 h / -75 - -70 °C

4: 22 percent / zinc-lead, iodine / diethyl ether; benzene / 0.5 h / Heating

5: 59 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 50 h / 40 °C

With lead; sodium azide; phosphate buffer; iodine; diisobutylaluminium hydride; triphenylphosphine; zinc; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; hexane; water; benzene;

DOI:10.1021/jo960972i

Reference yield:

(E)-2-methyl-4-phenyl-3-butenoic acid methyl ester (33599-85-8) → 2,4-Dinitro-benzoic acid (E)-(1S,2R)-1-((E)-3-tert-butoxycarbonyl-allyl)-2-methyl-4-phenyl-but-3-enyl ester (182486-11-9)

Guidance literature:

Multi-step reaction with 4 steps

1: phosphate buffer, sodium azide / H₂O / 120 h / 25 °C / 2-propanol-treated Candida rugosa lipase presence, pH 7.0

2: 95 percent / diisobutylaluminum hydride / diethyl ether; hexane / 3 h / -75 - -70 °C

3: 22 percent / zinc-lead, iodine / diethyl ether; benzene / 0.5 h / Heating

4: 59 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 50 h / 40 °C

With lead; sodium azide; phosphate buffer; iodine; diisobutylaluminium hydride; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; hexane; water; benzene;

DOI:10.1021/jo960972i

upstream raw materials:

2,4-dinitrobenzoic acid

(2E,7E)-(5R,6R)-5-Hydroxy-6-methyl-8-phenyl-octa-2,7-dienoic acid tert-butyl ester

(E)-methyl 4-phenylbut-3-enoate

(E)-2-methyl-4-phenyl-3-butenoic acid methyl ester

Downstream raw materials:

cryptophycin C

cryptophycin-1

tert-butyl (5S,6R)-5-[(2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]-2-methylpropionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate

tert-butyl (5S,6R,2E,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoate

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