(2E,3E,5E,7E,9E)-2-ethylidene-11-{(1R,4S,5R)-4-(2-hydroxyethyl)-2-oxo-4-[2-(phenylselanyl)ethoxy]-6-oxa-3-azabicyclo[3.1.0]hex-1-yl}-4,10-dimethyl-11-oxoundeca-3,5,7,9-tetraenoic acid methyl ester

Base Information

• Chemical Name: (2E,3E,5E,7E,9E)-2-ethylidene-11-{(1R,4S,5R)-4-(2-hydroxyethyl)-2-oxo-4-[2-(phenylselanyl)ethoxy]-6-oxa-3-azabicyclo[3.1.0]hex-1-yl}-4,10-dimethyl-11-oxoundeca-3,5,7,9-tetraenoic acid methyl ester
• CAS No.: 858536-73-9
• Molecular Formula: C₃₀H₃₅NO₇Se
• Molecular Weight: 600.57
• Mol file: 858536-73-9.mol

Synonyms:(2E,3E,5E,7E,9E)-2-ethylidene-11-{(1R,4S,5R)-4-(2-hydroxyethyl)-2-oxo-4-[2-(phenylselanyl)ethoxy]-6-oxa-3-azabicyclo[3.1.0]hex-1-yl}-4,10-dimethyl-11-oxoundeca-3,5,7,9-tetraenoic acid methyl ester

Chemical Property of (2E,3E,5E,7E,9E)-2-ethylidene-11-{(1R,4S,5R)-4-(2-hydroxyethyl)-2-oxo-4-[2-(phenylselanyl)ethoxy]-6-oxa-3-azabicyclo[3.1.0]hex-1-yl}-4,10-dimethyl-11-oxoundeca-3,5,7,9-tetraenoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,3E,5E,7E,9E)-2-ethylidene-11-{(1R,4S,5R)-4-(2-hydroxyethyl)-2-oxo-4-[2-(phenylselanyl)ethoxy]-6-oxa-3-azabicyclo[3.1.0]hex-1-yl}-4,10-dimethyl-11-oxoundeca-3,5,7,9-tetraenoic acid methyl ester

There total 1 articles about (2E,3E,5E,7E,9E)-2-ethylidene-11-{(1R,4S,5R)-4-(2-hydroxyethyl)-2-oxo-4-[2-(phenylselanyl)ethoxy]-6-oxa-3-azabicyclo[3.1.0]hex-1-yl}-4,10-dimethyl-11-oxoundeca-3,5,7,9-tetraenoic 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: 31.0%

2-(phenylselenyl)ethanol (65275-32-3) + NG-391 (185850-14-0) → (2E,3E,5E,7E,9E)-2-ethylidene-11-{(1R,4S,5R)-4-(2-hydroxyethyl)-2-oxo-4-[2-(phenylselanyl)ethoxy]-6-oxa-3-azabicyclo[3.1.0]hex-1-yl}-4,10-dimethyl-11-oxoundeca-3,5,7,9-tetraenoic acid methyl ester (858536-73-9)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1002/anie.200500060

Reference yield: 73.0%

(2E,3E,5E,7E,9E)-2-ethylidene-11-{(1R,4S,5R)-4-(2-hydroxyethyl)-2-oxo-4-[2-(phenylselanyl)ethoxy]-6-oxa-3-azabicyclo[3.1.0]hex-1-yl}-4,10-dimethyl-11-oxoundeca-3,5,7,9-tetraenoic acid methyl ester (858536-73-9) + di-tert-butyl dicarbonate (24424-99-5) → (1R,4S,5R)-4-{2-[(tert-butoxycarbonyl)oxy]ethyl}-1-[(2E,4E,6E,8E,10E)-10-(methoxycarbonyl)-2,8-dimethyldodeca-2,4,6,8,10-pentaenoyl]-2-oxo-4-[2-(phenylselanyl)ethoxy]-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (858536-79-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1002/anie.200500060

Reference yield:

(2E,3E,5E,7E,9E)-2-ethylidene-11-{(1R,4S,5R)-4-(2-hydroxyethyl)-2-oxo-4-[2-(phenylselanyl)ethoxy]-6-oxa-3-azabicyclo[3.1.0]hex-1-yl}-4,10-dimethyl-11-oxoundeca-3,5,7,9-tetraenoic acid methyl ester (858536-73-9) → (2E,3E,5E,7E,9E)-2-ethylidene-4,10-dimethyl-11-oxo-11-{(3aS,6S,6aR)-5-oxo-3a-[2-(phenylselanyl)ethoxy]hexahydro-2H-furo[3,2-b]pyrrol-6-yl}undeca-3,5,7,9-tetraenoic acid methyl ester (858536-91-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: 14.5 mg / SmI₂ / tetrahydrofuran / 0.67 h / -78 °C

3: 36 percent / CF₃COOH / CH₂Cl₂ / 2.5 h / 20 °C

With dmap; samarium diiodide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.200500060

upstream raw materials:

2-(phenylselenyl)ethanol

NG-391

Downstream raw materials:

(1R,4S,5R)-4-{2-[(tert-butoxycarbonyl)oxy]ethyl}-1-[(2E,4E,6E,8E,10E)-10-(methoxycarbonyl)-2,8-dimethyldodeca-2,4,6,8,10-pentaenoyl]-2-oxo-4-[2-(phenylselanyl)ethoxy]-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

(2E,3E,5E,7E,9E)-2-ethylidene-4,10-dimethyl-11-oxo-11-{(3aS,6S,6aR)-5-oxo-3a-[2-(phenylselanyl)ethoxy]hexahydro-2H-furo[3,2-b]pyrrol-6-yl}undeca-3,5,7,9-tetraenoic acid methyl ester

C₃₀H₃₅NO₇Se

(2S)-2-{2-[(tert-butoxycarbonyl)oxy]ethyl}-4-[(2E,4E,6E,8E,10E)-10-(methoxycarbonyl)-2,8-dimethyldodeca-2,4,6,8,10-pentaenoyl]-5-oxo-2-[2-(phenylselanyl)ethoxy]-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester