(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

Base Information

• Chemical Name: (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
• CAS No.: 206661-19-0
• Molecular Formula: C₃₉H₅₅NO₈
• Molecular Weight: 665.868
• Mol file: 206661-19-0.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 25 articles about (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 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:

(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 (170707-66-1) → (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 (206661-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. LiOH / methanol; tetrahydrofuran / 48 h / Ambient temperature

2: iPr₂NEt, N,N'-bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C

With lithium hydroxide; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; toluene;

DOI:10.1021/ja974318b

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) → (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 (206661-19-0)

Guidance literature:

Multi-step reaction with 6 steps

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

2: 1.) (COCl)2, DMSO, 2.) Et₃N

3: 97 percent / toluene / 12 h / Heating

4: 99 percent / NaBH₂S₃ / tetrahydrofuran / 5 h / Heating

5: aq. LiOH / methanol; tetrahydrofuran / 48 h / Ambient temperature

6: iPr₂NEt, N,N'-bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C

With lithium hydroxide; oxalyl dichloride; NaBH₂S₃; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; toluene;

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) → (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 (206661-19-0)

Guidance literature:

Multi-step reaction with 7 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

3: 1.) (COCl)2, DMSO, 2.) Et₃N

4: 97 percent / toluene / 12 h / Heating

5: 99 percent / NaBH₂S₃ / tetrahydrofuran / 5 h / Heating

6: aq. LiOH / methanol; tetrahydrofuran / 48 h / Ambient temperature

7: iPr₂NEt, N,N'-bis(2-oxo-3-oxazolidinyl)phosphinic chloride / toluene / 12 h / 85 °C

With lithium hydroxide; oxalyl dichloride; 18-crown-6 ether; NaBH₂S₃; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; toluene;

DOI:10.1021/ja974318b

upstream raw materials:

(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-dienal

(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

(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

Downstream raw materials:

macbecin I