ethyl (3R,4R,5S,6R)-4-acetamido-5,6-dihydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Base Information

Chemical Name:ethyl (3R,4R,5S,6R)-4-acetamido-5,6-dihydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
CAS No.:1196490-06-8
Molecular Formula:C₁₆H₂₇NO₆
Molecular Weight:329.393
Hs Code.:

Synonyms:ethyl (3R,4R,5S,6R)-4-acetamido-5,6-dihydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

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Chemical Property of ethyl (3R,4R,5S,6R)-4-acetamido-5,6-dihydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

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Technology Process of ethyl (3R,4R,5S,6R)-4-acetamido-5,6-dihydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

There total 6 articles about ethyl (3R,4R,5S,6R)-4-acetamido-5,6-dihydroxy-3-(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: 71.0%

: 1196490-01-3
ethyl (3aR,6R,7S,7aS)-7-acetamido-2,2-dimethyl-6-(pentan-3-yloxy)-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-4-carboxylate

: 1196490-06-8
ethyl (3R,4R,5S,6R)-4-acetamido-5,6-dihydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Guidance literature:: ethyl (3aR,6R,7S,7aS)-7-acetamido-2,2-dimethyl-6-(pentan-3-yloxy)-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-4-carboxylate; With hydrogenchloride; In ethanol; at 20 - 60 ℃; for 5h;

With water; at 60 ℃; for 1h;

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

: 1196490-06-8
ethyl (3R,4R,5S,6R)-4-acetamido-5,6-dihydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 3 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

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(II) bis(trifluoromethanesulfonate); triethylamine; In ethanol; water; toluene;
DOI:10.1021/jo2018872

Reference yield:

: 1062100-75-7
N-((3aS,4S,5R,7aS)-7-bromo-2,2-dimethyl-5-(pentan-3-yloxy)-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxol-4-yl)acetamide

: 1196490-06-8
ethyl (3R,4R,5S,6R)-4-acetamido-5,6-dihydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 4 h / Reflux; Inert atmosphere

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

2.2: 1 h / 60 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In ethanol; water; toluene;
DOI:10.1021/jo2018872