(2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(2,5-Dimethoxy-3-nitro-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester

Base Information

• Chemical Name: (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(2,5-Dimethoxy-3-nitro-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester
• CAS No.: 170707-65-0
• Molecular Formula: C₄₁H₅₉NO₁₁
• Molecular Weight: 741.92

Synonyms:(2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(2,5-Dimethoxy-3-nitro-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester

Chemical Property of (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(2,5-Dimethoxy-3-nitro-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester

Chemical Property:

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Technology Process of (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(2,5-Dimethoxy-3-nitro-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester

There total 23 articles about (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(2,5-Dimethoxy-3-nitro-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl 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: 97.0%

(2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-13-(2,5-Dimethoxy-3-nitro-phenyl)-9,10,13-trimethoxy-5-(4-methoxy-benzyloxy)-4,6,8,12-tetramethyl-trideca-2,6-dienal (170707-64-9) + (carbethoxyethylidene)triphenylphosphorane (21382-82-1) → (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(2,5-Dimethoxy-3-nitro-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester (170707-65-0)

Guidance literature:

In toluene; Heating;

DOI:10.1021/ja00147a027

Reference yield:

(2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-13-(2,5-Dimethoxy-3-nitro-phenyl)-9,10,13-trimethoxy-5-(4-methoxy-benzyloxy)-4,6,8,12-tetramethyl-trideca-2,6-dienoic acid methyl ester (170707-62-7) → (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(2,5-Dimethoxy-3-nitro-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester (170707-65-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / DIBAL / tetrahydrofuran / -78 °C

2: 1.) (COCl)2, DMSO, 2.) Et₃N

3: 97 percent / toluene / 12 h / Heating

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1021/ja974318b

Reference yield:

2,5-Dimethoxy-1-nitro-3-[(7E,11E)-(1R,2S,4S,5R,6S,9R,10S)-1,4,5,14-tetramethoxy-9-(4-methoxy-benzyloxy)-2,6,8,10-tetramethyl-tetradeca-7,11-dienyl]-benzene (170707-60-5) → (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(2,5-Dimethoxy-3-nitro-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester (170707-65-0)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. OsO₄, NMO / 2-methyl-propan-2-ol; tetrahydrofuran / Ambient temperature

2: Pb(OAc)4, K₂CO₃ / benzene / 0.08 h / Ambient temperature

3: 1.) KN(TMS)2, 18-crown-6 ether / 1.) THF, toluene, -78 deg C, 5 min, 2.) THF, toluene, -78 deg C, 3 h

4: 87 percent / DIBAL / tetrahydrofuran / -78 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N

6: 97 percent / toluene / 12 h / Heating

With lead(IV) acetate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/ja974318b

upstream raw materials:

(2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-13-(2,5-Dimethoxy-3-nitro-phenyl)-9,10,13-trimethoxy-5-(4-methoxy-benzyloxy)-4,6,8,12-tetramethyl-trideca-2,6-dienal

(carbethoxyethylidene)triphenylphosphorane

(E)-(2R,3R,6S,7R,8S,10S,11R)-11-(2,5-Dimethoxy-3-nitro-phenyl)-7,8,11-trimethoxy-3-(4-methoxy-benzyloxy)-2,4,6,10-tetramethyl-undec-4-enal

(2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-13-(2,5-Dimethoxy-3-nitro-phenyl)-9,10,13-trimethoxy-5-(4-methoxy-benzyloxy)-4,6,8,12-tetramethyl-trideca-2,6-dien-1-ol

Downstream raw materials:

(2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxy-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester

macbecin I

(4E,6Z,10E)-(8S,9R,12S,13R,14S,16S,17R)-13,14,17,20,22-Pentamethoxy-9-(4-methoxy-benzyloxy)-4,8,10,12,16-pentamethyl-2-aza-bicyclo[16.3.1]docosa-1⁽²²⁾,4,6,10,18,20-hexaen-3-one

(2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxy-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid

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