(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

Base Information

• Chemical Name: (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
• CAS No.: 858536-79-5
• Molecular Formula: C₄₀H₅₁NO₁₁Se
• Molecular Weight: 800.805
• Mol file: 858536-79-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 3 articles about (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 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: 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:

2-(phenylselenyl)ethanol (65275-32-3) → (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:

Multi-step reaction with 2 steps

1: 31 percent / TsOH*H₂O / CH₂Cl₂ / 3 h / 20 °C

2: 73 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

With dmap; toluene-4-sulfonic acid; triethylamine; In dichloromethane;

DOI:10.1002/anie.200500060

Reference yield:

NG-391 (185850-14-0) → (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:

Multi-step reaction with 2 steps

1: 31 percent / TsOH*H₂O / CH₂Cl₂ / 3 h / 20 °C

2: 73 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

With dmap; toluene-4-sulfonic acid; triethylamine; In dichloromethane;

DOI:10.1002/anie.200500060

upstream raw materials:

(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

di-tert-butyl dicarbonate

2-(phenylselenyl)ethanol

NG-391

Downstream raw materials:

(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

(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