(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

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-dien-1-ol
• CAS No.: 206661-17-8
• Molecular Formula: C₃₆H₅₃NO₁₀
• Molecular Weight: 659.818
• Mol file: 206661-17-8.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-dien-1-ol

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-dien-1-ol

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-dien-1-ol

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-dien-1-ol 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: 87.0%

(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-dienoic acid methyl ester (170707-62-7) → (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 (206661-17-8)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/ja00147a027 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) → (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 (206661-17-8)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/ja974318b

Reference yield:

(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-dien-1-ol (206661-17-8)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 87 percent / DIBAL / tetrahydrofuran / -78 °C

With 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran;

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-dienoic acid methyl ester

(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:

(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

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