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

Base Information

• Chemical Name: 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
• CAS No.: 170707-59-2
• Molecular Formula: C₃₇H₅₅NO₁₀
• Molecular Weight: 673.844
• Mol file: 170707-59-2.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 1 articles about 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 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: 89.0%

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 → 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 (170707-59-2)

Guidance literature:

With methanol; potassium carbonate;

DOI:10.1021/ja974318b

Reference yield: 92.0%

methyl trifluoromethanesulfonate (333-27-7) + 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 (170707-59-2) → 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)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 5h;

DOI:10.1021/ja974318b

Reference yield:

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 (170707-59-2) → (2E,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-2,8-dienoic acid ethyl ester

Guidance literature:

Multi-step reaction with 8 steps

1: 92 percent / t-BuOK / dimethylformamide / 5 h / 0 - 20 °C

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

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

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

5: 87 percent / DIBAL / tetrahydrofuran / -78 °C

6: 1.) (COCl)2, DMSO, 2.) Et₃N

7: 97 percent / toluene / 12 h / Heating

8: 100 percent / H₂, quinoline / Pd(CaCO₃)PbO / ethanol

With quinoline; lead(IV) acetate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; 18-crown-6 ether; potassium tert-butylate; hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; Lindlar's catalyst; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/ja974318b

Downstream raw materials:

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

macbecin I

(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

(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