(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

Base Information

• Chemical Name: (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
• CAS No.: 170707-62-7
• Molecular Formula: C₃₇H₅₃NO₁₁
• Molecular Weight: 687.828
• Mol file: 170707-62-7.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 21 articles about (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 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:

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) + (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 (170707-61-6) → (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)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/ja00147a027

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) → (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)

Guidance literature:

Multi-step reaction with 3 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

With lead(IV) acetate; osmium(VIII) oxide; N-methyl-2-indolinone; 18-crown-6 ether; potassium hexamethylsilazane; potassium carbonate; In tetrahydrofuran; tert-butyl alcohol; benzene;

DOI:10.1021/ja974318b

Reference yield:

Acetic acid 4-[(E)-(4S,5R,6S,8S,9R)-9-(2,5-dimethoxy-3-nitro-phenyl)-5,6,9-trimethoxy-1-((E)-(S)-5-methoxy-1-methyl-pent-2-enyl)-2,4,8-trimethyl-non-2-enyloxymethyl]-phenyl ester → (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)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / K₂CO₃, MeOH

2: 92 percent / t-BuOK / dimethylformamide / 5 h / 0 - 20 °C

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

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

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

With lead(IV) acetate; methanol; osmium(VIII) oxide; N-methyl-2-indolinone; 18-crown-6 ether; potassium tert-butylate; potassium hexamethylsilazane; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1021/ja974318b

upstream raw materials:

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

(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

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

4-[(E)-(1R,4S,5R,6S,8S,9R)-9-(2,5-Dimethoxy-3-nitro-phenyl)-5,6,9-trimethoxy-1-((E)-(S)-5-methoxy-1-methyl-pent-2-enyl)-2,4,8-trimethyl-non-2-enyloxymethyl]-phenol

Downstream raw materials:

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

(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

(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