ethyl (4S,5R,6S)-7-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-((tert-butoxycarbonyl)amino)-5-hydroxy-7-oxo-6-(pentan-3-yloxy)heptanoate

Base Information

Chemical Name:ethyl (4S,5R,6S)-7-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-((tert-butoxycarbonyl)amino)-5-hydroxy-7-oxo-6-(pentan-3-yloxy)heptanoate
CAS No.:1344715-86-1
Molecular Formula:C₂₉H₄₄N₂O₉
Molecular Weight:564.676
Hs Code.:

Synonyms:ethyl (4S,5R,6S)-7-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-((tert-butoxycarbonyl)amino)-5-hydroxy-7-oxo-6-(pentan-3-yloxy)heptanoate

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Chemical Property of ethyl (4S,5R,6S)-7-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-((tert-butoxycarbonyl)amino)-5-hydroxy-7-oxo-6-(pentan-3-yloxy)heptanoate

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Technology Process of ethyl (4S,5R,6S)-7-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-((tert-butoxycarbonyl)amino)-5-hydroxy-7-oxo-6-(pentan-3-yloxy)heptanoate

There total 4 articles about ethyl (4S,5R,6S)-7-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-((tert-butoxycarbonyl)amino)-5-hydroxy-7-oxo-6-(pentan-3-yloxy)heptanoate 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: 45.0%

: 1029289-25-5
ethyl (S)-4-(tert-butoxycarbonylamino)-5-oxopentanoate

: 1344715-84-9
(S)-4-benzyl-3-(2-(pent-3-yloxy)acetyl)oxazolidin-2-one

: 1344715-86-1
ethyl (4S,5R,6S)-7-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-((tert-butoxycarbonyl)amino)-5-hydroxy-7-oxo-6-(pentan-3-yloxy)heptanoate

Guidance literature:: (S)-4-benzyl-3-(2-(pent-3-yloxy)acetyl)oxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 - 0 ℃; for 2h;

ethyl (S)-4-(tert-butoxycarbonylamino)-5-oxopentanoate; In dichloromethane; at -78 - -30 ℃; for 4.25h; stereoselective reaction;
DOI:10.1039/c1ob06248d

Reference yield:

: 65487-73-2
(S)-2-((tert-butoxycarbonyl)amino)-5-ethoxy-5-oxopentanoic acid

: 1344715-86-1
ethyl (4S,5R,6S)-7-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-((tert-butoxycarbonyl)amino)-5-hydroxy-7-oxo-6-(pentan-3-yloxy)heptanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine; isobutyl chloroformate / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

1.2: 1.25 h / 0 - 20 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine; triethylsilane; palladium 10% on activated carbon / acetone / 1.25 h / 20 °C / Inert atmosphere

3.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / 2 h / -78 - 0 °C

3.2: 4.25 h / -78 - -30 °C

With 2,6-dimethylpyridine; triethylsilane; di-n-butylboryl trifluoromethanesulfonate; palladium 10% on activated carbon; triethylamine; isobutyl chloroformate; In dichloromethane; acetone;
DOI:10.1039/c1ob06248d

Reference yield:

: 189955-91-7
2-(pentan-3-yloxy)acetic acid

: 1344715-86-1
ethyl (4S,5R,6S)-7-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-((tert-butoxycarbonyl)amino)-5-hydroxy-7-oxo-6-(pentan-3-yloxy)heptanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: pivaloyl chloride; triethylamine / diethyl ether / 1.08 h / -78 - 0 °C / Inert atmosphere

1.2: 0.5 h / -78 - 0 °C / Inert atmosphere

2.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / 2 h / -78 - 0 °C

2.2: 4.25 h / -78 - -30 °C

With di-n-butylboryl trifluoromethanesulfonate; pivaloyl chloride; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1039/c1ob06248d