2-[(2R,10S,12S)-10-{2-[(2R)-4-iodo-2-methoxybut-3-enyl]oxazol-4-oyloxy}-2-methoxy-12-(4-methoxybenzyloxy)-11,11-dimethylpentadeca-3,7,13-trien-5-ynyl]-oxazole-4-carboxylic acid methyl ester

Base Information

Chemical Name:2-[(2R,10S,12S)-10-{2-[(2R)-4-iodo-2-methoxybut-3-enyl]oxazol-4-oyloxy}-2-methoxy-12-(4-methoxybenzyloxy)-11,11-dimethylpentadeca-3,7,13-trien-5-ynyl]-oxazole-4-carboxylic acid methyl ester
CAS No.:809285-76-5
Molecular Formula:C₄₀H₄₇IN₂O₁₀
Molecular Weight:842.725
Hs Code.:

2-[(2R,10S,12S)-10-{2-[(2R)-4-iodo-2-methoxybut-3-enyl]oxazol-4-oyloxy}-2-methoxy-12-(4-methoxybenzyloxy)-11,11-dimethylpentadeca-3,7,13-trien-5-ynyl]-oxazole-4-carboxylic acid methyl ester

Synonyms:2-[(2R,10S,12S)-10-{2-[(2R)-4-iodo-2-methoxybut-3-enyl]oxazol-4-oyloxy}-2-methoxy-12-(4-methoxybenzyloxy)-11,11-dimethylpentadeca-3,7,13-trien-5-ynyl]-oxazole-4-carboxylic acid methyl ester

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Chemical Property of 2-[(2R,10S,12S)-10-{2-[(2R)-4-iodo-2-methoxybut-3-enyl]oxazol-4-oyloxy}-2-methoxy-12-(4-methoxybenzyloxy)-11,11-dimethylpentadeca-3,7,13-trien-5-ynyl]-oxazole-4-carboxylic acid methyl ester

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Technology Process of 2-[(2R,10S,12S)-10-{2-[(2R)-4-iodo-2-methoxybut-3-enyl]oxazol-4-oyloxy}-2-methoxy-12-(4-methoxybenzyloxy)-11,11-dimethylpentadeca-3,7,13-trien-5-ynyl]-oxazole-4-carboxylic acid methyl ester

There total 22 articles about 2-[(2R,10S,12S)-10-{2-[(2R)-4-iodo-2-methoxybut-3-enyl]oxazol-4-oyloxy}-2-methoxy-12-(4-methoxybenzyloxy)-11,11-dimethylpentadeca-3,7,13-trien-5-ynyl]-oxazole-4-carboxylic 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: 80.0%

: 809285-74-3
2-[(2R)-4-iodo-2-methoxybut-3-enyl]oxazole-4-carboxylic acid

: 809285-75-4
2-{(2R,10S,12S)-[10-hydroxy-2-methoxy-12-(4-methoxybenzyloxy)-11,11-dimethylpentadeca-3,7,13-trien-5-ynyl]}-oxazole-4-carboxylic acid methyl ester

: 809285-76-5
2-[(2R,10S,12S)-10-{2-[(2R)-4-iodo-2-methoxybut-3-enyl]oxazol-4-oyloxy}-2-methoxy-12-(4-methoxybenzyloxy)-11,11-dimethylpentadeca-3,7,13-trien-5-ynyl]-oxazole-4-carboxylic acid methyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 14h;
DOI:10.1021/ja0443068

Reference yield:

: 286372-15-4
(3R)-3-methoxypent-4-ynoic acid

: 809285-76-5
2-[(2R,10S,12S)-10-{2-[(2R)-4-iodo-2-methoxybut-3-enyl]oxazol-4-oyloxy}-2-methoxy-12-(4-methoxybenzyloxy)-11,11-dimethylpentadeca-3,7,13-trien-5-ynyl]-oxazole-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 55 percent / 1-hydroxybenzotriazole; EDC; N-methylmorpholine / CH₂Cl₂ / 16 h / 20 °C

2.1: diethylaminosulfurtrifluoride / CH₂Cl₂ / 1 h / -78 °C

2.2: K₂CO₃ / CH₂Cl₂ / 0.67 h / -78 - 0 °C

2.3: 106.3 mg / BrCCl₃; DBU / CH₂Cl₂ / 20 h / 4 °C

3.1: 54 percent / AgNO₃; N-bromosuccinimide / acetone / 1 h / 20 °C

4.1: PdCl₂(PPh₃)2; n-Bu₄SnH / tetrahydrofuran / 3.5 h / -78 - 0 °C

4.2: 92 percent / I₂ / tetrahydrofuran

5.1: 94 percent / PdCl₂(PPh₃)2; CuI; Et₃N / acetonitrile / cooling

6.1: 80 percent / DMAP; dicyclohexylcarbodiimide / CH₂Cl₂ / 14 h / 20 °C

With 4-methyl-morpholine; dmap; bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; copper(l) iodide; diethylamino-sulfur trifluoride; n-Bu₄SnH; benzotriazol-1-ol; silver nitrate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetone; acetonitrile; 5.1: Sonogashira cross-coupling / 6.1: Sonogashira coupling;
DOI:10.1021/ja0443068

Reference yield:

: 809285-65-2
(3R)-5-(triisopropylsilyloxy)-1-(trimethylsilyl)pent-1-yn-3-ol

: 809285-76-5
2-[(2R,10S,12S)-10-{2-[(2R)-4-iodo-2-methoxybut-3-enyl]oxazol-4-oyloxy}-2-methoxy-12-(4-methoxybenzyloxy)-11,11-dimethylpentadeca-3,7,13-trien-5-ynyl]-oxazole-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / aq. NaOH; n-Bu₄NHSO₄ / toluene / 3.5 h / 0 - 20 °C

2.1: aq. HF / acetonitrile / 24 h / 20 °C

2.2: 99 percent / TEMPO; NaClO₂; NaOCl / aq. phosphate buffer; acetonitrile / 18 h / pH 6.7 / Heating

3.1: 55 percent / 1-hydroxybenzotriazole; EDC; N-methylmorpholine / CH₂Cl₂ / 16 h / 20 °C

4.1: diethylaminosulfurtrifluoride / CH₂Cl₂ / 1 h / -78 °C

4.2: K₂CO₃ / CH₂Cl₂ / 0.67 h / -78 - 0 °C

4.3: 106.3 mg / BrCCl₃; DBU / CH₂Cl₂ / 20 h / 4 °C

5.1: 54 percent / AgNO₃; N-bromosuccinimide / acetone / 1 h / 20 °C

6.1: PdCl₂(PPh₃)2; n-Bu₄SnH / tetrahydrofuran / 3.5 h / -78 - 0 °C

6.2: 92 percent / I₂ / tetrahydrofuran

7.1: 94 percent / PdCl₂(PPh₃)2; CuI; Et₃N / acetonitrile / cooling

8.1: 80 percent / DMAP; dicyclohexylcarbodiimide / CH₂Cl₂ / 14 h / 20 °C

With 4-methyl-morpholine; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; N-Bromosuccinimide; copper(l) iodide; diethylamino-sulfur trifluoride; n-Bu₄SnH; hydrogen fluoride; tetra(n-butyl)ammonium hydrogensulfate; benzotriazol-1-ol; silver nitrate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; acetone; toluene; acetonitrile; 7.1: Sonogashira cross-coupling / 8.1: Sonogashira coupling;
DOI:10.1021/ja0443068