ethyl (3S,4R,5R)-4-acetamido-3-amino-5-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

Base Information

Chemical Name:ethyl (3S,4R,5R)-4-acetamido-3-amino-5-(pentan-3-yloxy)-cyclohex-1-enecarboxylate
CAS No.:1052063-39-4
Molecular Formula:C₁₆H₂₈N₂O₄
Molecular Weight:312.409
Hs Code.:

Synonyms:ethyl (3S,4R,5R)-4-acetamido-3-amino-5-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

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Chemical Property of ethyl (3S,4R,5R)-4-acetamido-3-amino-5-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

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Technology Process of ethyl (3S,4R,5R)-4-acetamido-3-amino-5-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

There total 12 articles about ethyl (3S,4R,5R)-4-acetamido-3-amino-5-(pentan-3-yloxy)-cyclohex-1-enecarboxylate 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: 9.0%

: 1196490-17-1
ethyl (3R,4R,5R,6R)-4-acetamido-5-azido-6-(methylsulfonyloxy)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

: 1196490-21-7
C₁₆H₂₇NO₄

: 1052063-39-4
ethyl (3S,4R,5R)-4-acetamido-3-amino-5-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1021/jo2018872

Reference yield:

: 1196490-17-1
ethyl (3R,4R,5R,6R)-4-acetamido-5-azido-6-(methylsulfonyloxy)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

: 1196490-21-7
C₁₆H₂₇NO₄

: 1052063-39-4
ethyl (3S,4R,5R)-4-acetamido-3-amino-5-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

: 196618-13-0
oseltamivir

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at -30 - 20 ℃;

Reference yield:

: 1056467-86-7
(3aS,4S,5S,7aS)-8-acetyl-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-4,5-epimino-1,3-benzodioxole

: 1196490-21-7
C₁₆H₂₇NO₄

: 1052063-39-4
ethyl (3S,4R,5R)-4-acetamido-3-amino-5-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: copper(II) bis(trifluoromethanesulfonate) / 16 h / 0 °C / Inert atmosphere; Neat (no solvent)

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / ethanol; toluene / 2 h / 60 °C / 760.05 Torr / Inert atmosphere

2.2: 4 h / Reflux; Inert atmosphere

3.1: hydrogenchloride / ethanol; water / 5 h / 60 °C

3.2: 1 h / 60 °C

4.1: pyridine / 48 h / 20 °C / Inert atmosphere

5.1: tetrabutylammoniun azide / 1,2-dimethoxyethane / 16 h / Reflux; Inert atmosphere

6.1: triethylamine / dichloromethane / 3 h / -78 - 15 °C / Inert atmosphere

7.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 12 h / 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammoniun azide; copper(II) bis(trifluoromethanesulfonate); triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; toluene;
DOI:10.1021/jo2018872