(3E,5E,13E,19E)-(1R,9S,10R,11S,15R,17R,21S,24R,25R,27S,29R)-11-Hydroxy-15,21-dimethoxy-27-(4-methoxy-phenyl)-10,17,20,24,29-pentamethyl-9-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-8,26,28-trioxa-bicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-one

Base Information

• Chemical Name: (3E,5E,13E,19E)-(1R,9S,10R,11S,15R,17R,21S,24R,25R,27S,29R)-11-Hydroxy-15,21-dimethoxy-27-(4-methoxy-phenyl)-10,17,20,24,29-pentamethyl-9-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-8,26,28-trioxa-bicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-one
• CAS No.: 213390-88-6
• Molecular Formula: C₅₂H₈₆O₉Si
• Molecular Weight: 883.335
• Mol file: 213390-88-6.mol

Synonyms:(3E,5E,13E,19E)-(1R,9S,10R,11S,15R,17R,21S,24R,25R,27S,29R)-11-Hydroxy-15,21-dimethoxy-27-(4-methoxy-phenyl)-10,17,20,24,29-pentamethyl-9-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-8,26,28-trioxa-bicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-one

Chemical Property of (3E,5E,13E,19E)-(1R,9S,10R,11S,15R,17R,21S,24R,25R,27S,29R)-11-Hydroxy-15,21-dimethoxy-27-(4-methoxy-phenyl)-10,17,20,24,29-pentamethyl-9-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-8,26,28-trioxa-bicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3E,5E,13E,19E)-(1R,9S,10R,11S,15R,17R,21S,24R,25R,27S,29R)-11-Hydroxy-15,21-dimethoxy-27-(4-methoxy-phenyl)-10,17,20,24,29-pentamethyl-9-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-8,26,28-trioxa-bicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-one

There total 10 articles about (3E,5E,13E,19E)-(1R,9S,10R,11S,15R,17R,21S,24R,25R,27S,29R)-11-Hydroxy-15,21-dimethoxy-27-(4-methoxy-phenyl)-10,17,20,24,29-pentamethyl-9-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-8,26,28-trioxa-bicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-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: 79.0%

(2E,4E)-6-[(2S,4R,5R,6R)-6-((5E,11E)-(1R,4S,8R,10R,14S,15R,16S,17S)-14,16-Dihydroxy-4,10-dimethoxy-1,5,8,15,17-pentamethyl-18-triisopropylsilanyloxy-octadeca-5,11-dienyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-hexa-2,4-dienoic acid (213390-87-5) → (3E,5E,13E,19E)-(1R,9S,10R,11S,15R,17R,21S,24R,25R,27S,29R)-11-Hydroxy-15,21-dimethoxy-27-(4-methoxy-phenyl)-10,17,20,24,29-pentamethyl-9-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-8,26,28-trioxa-bicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-one (213390-88-6)

Guidance literature:

With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In chloroform; at 20 ℃; for 4h;

DOI:10.1016/S0040-4039(98)01192-7

Reference yield:

C60H104O9Si2 (210709-28-7) → (3E,5E,13E,19E)-(1R,9S,10R,11S,15R,17R,21S,24R,25R,27S,29R)-11-Hydroxy-15,21-dimethoxy-27-(4-methoxy-phenyl)-10,17,20,24,29-pentamethyl-9-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-8,26,28-trioxa-bicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-one (213390-88-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / sodium chlorite, NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 18 h / 20 °C

2: 90 percent / HF*pyr / pyridine; tetrahydrofuran / 20 °C

3: 79 percent / 2,4,6-trichlorobenzoyl chloride, DMAP, Et₃N / CHCl₃ / 4 h / 20 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2,4,6-trichlorobenzoyl chloride; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; pyridine; chloroform; water; tert-butyl alcohol;

DOI:10.1016/S0040-4039(98)01192-7

Reference yield:

C66H120O9Si3 (210709-24-3) → (3E,5E,13E,19E)-(1R,9S,10R,11S,15R,17R,21S,24R,25R,27S,29R)-11-Hydroxy-15,21-dimethoxy-27-(4-methoxy-phenyl)-10,17,20,24,29-pentamethyl-9-((S)-1-methyl-2-triisopropylsilanyloxy-ethyl)-8,26,28-trioxa-bicyclo[23.3.1]nonacosa-3,5,13,19-tetraen-7-one (213390-88-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / DDQ, pH₇ buffer / CH₂Cl₂ / 0.17 h / 0 °C

2: 91 percent / sodium chlorite, NaH₂PO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 18 h / 20 °C

3: 90 percent / HF*pyr / pyridine; tetrahydrofuran / 20 °C

4: 79 percent / 2,4,6-trichlorobenzoyl chloride, DMAP, Et₃N / CHCl₃ / 4 h / 20 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; pH₇ buffer; 2,4,6-trichlorobenzoyl chloride; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; pyridine; dichloromethane; chloroform; water; tert-butyl alcohol;

DOI:10.1016/S0040-4039(98)01192-7

upstream raw materials:

(2E,4E)-6-[(2S,4R,5R,6R)-6-((5E,11E)-(1R,4S,8R,10R,14S,15R,16S,17S)-14,16-Dihydroxy-4,10-dimethoxy-1,5,8,15,17-pentamethyl-18-triisopropylsilanyloxy-octadeca-5,11-dienyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-hexa-2,4-dienoic acid

C₆₀H₁₀₄O₉Si₂

C₆₆H₁₂₀O₉Si₃

(2E,4E)-6-[(2S,4R,5R,6S)-6-((S)-2-Iodo-1-methyl-ethyl)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-hexa-2,4-dienoic acid methyl ester