(2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-9,10,13-trimethoxy-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)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-9,10,13-trimethoxy-4,6,8,12-tetramethyl-trideca-2,6-dienoic acid methyl ester
• CAS No.: 123083-94-3
• Molecular Formula: C₄₁H₆₇NO₈Si
• Molecular Weight: 730.07
• Mol file: 123083-94-3.mol

Synonyms:(2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-9,10,13-trimethoxy-4,6,8,12-tetramethyl-trideca-2,6-dienoic acid methyl ester

Chemical Property of (2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-9,10,13-trimethoxy-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)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-9,10,13-trimethoxy-4,6,8,12-tetramethyl-trideca-2,6-dienoic acid methyl ester

There total 19 articles about (2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-9,10,13-trimethoxy-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: 99.0%

(E)-(2R,3R,6S,7R,8S,10S,11R)-3-(tert-Butyl-dimethyl-silanyloxy)-11-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-7,8,11-trimethoxy-2,4,6,10-tetramethyl-undec-4-enal (123084-07-1) + bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) → (2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-9,10,13-trimethoxy-4,6,8,12-tetramethyl-trideca-2,6-dienoic acid methyl ester (123083-94-3)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1039/c39890000378

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-9,10,13-trimethoxy-4,6,8,12-tetramethyl-trideca-2,6-dienoic acid methyl ester (123083-94-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

2: 98 percent / di-isobutyl aluminium hydride / toluene / 1.5 h / -20 °C

3: 99 percent / imidazole / dimethylformamide / 17 h / 25 °C

4: 1.) T-BuLi, CuCN; 2.) BF₃OEt₂*OEt₂ / 1.) Et₂O, -80 deg C, 2 h then -78 deg C to -10 deg C, 15 min; 2.) -78 deg C, 1 h

5: 96 percent / NaH / tetrahydrofuran / 6 h

6: 96 percent / HF*Py-Py-THF / methanol / 6.5 h / 25 °C

7: 89 percent / SO₃*Py, Et₃N / tetrahydrofuran; dimethylsulfoxide / 1.5 h / 25 °C

8: 99 percent / KN(SiMe₃)2, 18-crown-6 / tetrahydrofuran / 1 h / -78 °C

With tetrahydrofuran; pyridine; 1H-imidazole; 2,6-dimethylpyridine; 18-crown-6 ether; pyridine-SO₃ complex; boron trifluoride diethyl etherate; tert.-butyl lithium; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1039/c39890000378

Reference yield:

(E)-(3R,4S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-iodo-2,4-dimethyl-pent-1-ene (123083-92-1) → (2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-5-(tert-Butyl-dimethyl-silanyloxy)-13-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-9,10,13-trimethoxy-4,6,8,12-tetramethyl-trideca-2,6-dienoic acid methyl ester (123083-94-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) T-BuLi, CuCN; 2.) BF₃OEt₂*OEt₂ / 1.) Et₂O, -80 deg C, 2 h then -78 deg C to -10 deg C, 15 min; 2.) -78 deg C, 1 h

2: 96 percent / NaH / tetrahydrofuran / 6 h

3: 96 percent / HF*Py-Py-THF / methanol / 6.5 h / 25 °C

4: 89 percent / SO₃*Py, Et₃N / tetrahydrofuran; dimethylsulfoxide / 1.5 h / 25 °C

5: 99 percent / KN(SiMe₃)2, 18-crown-6 / tetrahydrofuran / 1 h / -78 °C

With tetrahydrofuran; pyridine; 18-crown-6 ether; pyridine-SO₃ complex; boron trifluoride diethyl etherate; tert.-butyl lithium; potassium hexamethylsilazane; sodium hydride; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; methanol; dimethyl sulfoxide;

DOI:10.1039/c39890000378

upstream raw materials:

(E)-(2R,3R,6S,7R,8S,10S,11R)-3-(tert-Butyl-dimethyl-silanyloxy)-11-[3-(2,5-dimethyl-pyrrol-1-yl)-2,5-dimethoxy-phenyl]-7,8,11-trimethoxy-2,4,6,10-tetramethyl-undec-4-enal

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

t-butyldimethylsiyl triflate

(E)-(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-2,4-dimethyl-pent-4-en-1-ol

Downstream raw materials:

(2Z,4S,5R,6E,8S,9R,10S,12S,13R)-5-tert-butyldimethylsilyloxy-13-<3'-(2'',5''-dimethylpyrrol-1''-yl)-2',5'-dimethoxy-phenyl>-9,10,13-trimethoxy-4,6,8,12-tetramethyl-2,6-tridecadien-1-ol

(2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-13-(3-Amino-2,5-dimethoxy-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-9,10,13-trimethoxy-4,6,8,12-tetramethyl-trideca-2,6-dien-1-ol

macbecin I

(2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxyphenyl)-7-(tert-butyldimethylsiloxy)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoic acid