{(E,Z)}-4-tert-butyldimethylsilyloxy-15,24-di(methoxymethoxy)-34-(p-methoxybenzyloxy)methyloxyasimicin-9-en-11-yne

Base Information

• Chemical Name: {(E,Z)}-4-tert-butyldimethylsilyloxy-15,24-di(methoxymethoxy)-34-(p-methoxybenzyloxy)methyloxyasimicin-9-en-11-yne
• CAS No.: 720678-51-3
• Molecular Formula: C₅₆H₉₂O₁₂Si
• Molecular Weight: 985.425

Synonyms:{(E,Z)}-4-tert-butyldimethylsilyloxy-15,24-di(methoxymethoxy)-34-(p-methoxybenzyloxy)methyloxyasimicin-9-en-11-yne

Chemical Property of {(E,Z)}-4-tert-butyldimethylsilyloxy-15,24-di(methoxymethoxy)-34-(p-methoxybenzyloxy)methyloxyasimicin-9-en-11-yne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(E,Z)}-4-tert-butyldimethylsilyloxy-15,24-di(methoxymethoxy)-34-(p-methoxybenzyloxy)methyloxyasimicin-9-en-11-yne

There total 32 articles about {(E,Z)}-4-tert-butyldimethylsilyloxy-15,24-di(methoxymethoxy)-34-(p-methoxybenzyloxy)methyloxyasimicin-9-en-11-yne 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: 83.0%

(2'R,5S)-3-[2'-(tert-butyldimethylsilyl)oxy-8'-iodooct-7'-enyl]-5-methyl-2,5-dihydrofuran-2-one (720678-27-3) + (5R,6R,9R,10R,13R,14R)-5,14-di(methoxymethoxy)-24-(p-methoxybenzyloxy)methoxy-6,9,10,13-dioxidotricos-1-yne (720678-26-2) → {(E,Z)}-4-tert-butyldimethylsilyloxy-15,24-di(methoxymethoxy)-34-(p-methoxybenzyloxy)methyloxyasimicin-9-en-11-yne (720678-51-3)

Guidance literature:

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; at 20 ℃; for 2h;

DOI:10.1002/chem.200305557

Reference yield:

(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one (184435-75-4) → {(E,Z)}-4-tert-butyldimethylsilyloxy-15,24-di(methoxymethoxy)-34-(p-methoxybenzyloxy)methyloxyasimicin-9-en-11-yne (720678-51-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran / 0.5 h

1.2: 50 percent / HMPA / tetrahydrofuran / 20 h / 20 °C

2.1: m-CPBA / CH₂Cl₂ / 0.33 h / 0 °C

3.1: 0.56 g / toluene / 2 h / Heating

4.1: aq. OsO₄ / tetrahydrofuran / 0.08 h

5.1: 0.185 g / NaIO₄ / tetrahydrofuran / 3 h

6.1: 60 percent / CrCl₂ / tetrahydrofuran / 4 h / 0 °C

7.1: 83 percent / Et₃N; CuI / (Ph₃P)2PdCl₂ / 2 h / 20 °C

With chromium dichloride; sodium periodate; copper(l) iodide; osmium(VIII) oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/chem.200305557

Reference yield:

1,7-Octadiene (3710-30-3) → {(E,Z)}-4-tert-butyldimethylsilyloxy-15,24-di(methoxymethoxy)-34-(p-methoxybenzyloxy)methyloxyasimicin-9-en-11-yne (720678-51-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 34 percent / aq. AD-mix-β / 2-methyl-propan-2-ol / 18 h / 0 °C

2.1: 65 percent / 2,4,6-collidine; DMAP / CH₂Cl₂ / 16 h / 0 - 20 °C

3.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

4.1: 95 percent / NaI; NaHCO₃ / acetone / 38 h / Heating

5.1: LDA / tetrahydrofuran / 0.5 h

5.2: 50 percent / HMPA / tetrahydrofuran / 20 h / 20 °C

6.1: m-CPBA / CH₂Cl₂ / 0.33 h / 0 °C

7.1: 0.56 g / toluene / 2 h / Heating

8.1: aq. OsO₄ / tetrahydrofuran / 0.08 h

9.1: 0.185 g / NaIO₄ / tetrahydrofuran / 3 h

10.1: 60 percent / CrCl₂ / tetrahydrofuran / 4 h / 0 °C

11.1: 83 percent / Et₃N; CuI / (Ph₃P)2PdCl₂ / 2 h / 20 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; chromium dichloride; dmap; sodium periodate; copper(l) iodide; osmium(VIII) oxide; AD-mix-β; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; acetone; toluene; tert-butyl alcohol;

DOI:10.1002/chem.200305557

upstream raw materials:

(2'R,5S)-3-[2'-(tert-butyldimethylsilyl)oxy-8'-iodooct-7'-enyl]-5-methyl-2,5-dihydrofuran-2-one

(5R,6R,9R,10R,13R,14R)-5,14-di(methoxymethoxy)-24-(p-methoxybenzyloxy)methoxy-6,9,10,13-dioxidotricos-1-yne

(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one

1,7-Octadiene

Downstream raw materials:

3-(4-Benzoyl-phenyl)-propionic acid (R)-11-{(2R,5R,2'R,5'R)-5'-[(1R,12R)-12-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-13-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-tridecyl]-octahydro-[2,2']bifuranyl-5-yl}-11-methoxymethoxy-undecyl ester

4-tert-butyldimethylsilyloxy-15,24-di(methoxymethoxy)-34-(p-methoxybenzyloxymethyloxy)asimicin

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