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

Base Information

Chemical Name:ethyl (3R,4R,5R,6R)-4-acetamido-5-azido-6-(methylsulfonyloxy)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
CAS No.:1196490-17-1
Molecular Formula:C₁₇H₂₈N₄O₇S
Molecular Weight:432.498
Hs Code.:

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

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

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

There total 10 articles about ethyl (3R,4R,5R,6R)-4-acetamido-5-azido-6-(methylsulfonyloxy)-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: 75.0%

: 1196491-58-3
ethyl (3R,4R,5R,6R)-4-acetamido-5-azido-6-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

: 124-63-0
methanesulfonyl chloride

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

Guidance literature:: With triethylamine; In dichloromethane; at -78 - 15 ℃; for 3h;

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

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

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 1106677-14-8
N-[(3aR,4R,5S,7aS)-4,7-dibromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-yl]acetamide

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

Guidance literature:: Multi-step reaction with 7 steps

1.1: tetrabutylammomium bromide; potassium hexamethylsilazane / 1,2-dimethoxyethane / 3 h / 0 °C / Inert atmosphere

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

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

3.2: 4 h / Reflux; Inert atmosphere

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

4.2: 1 h / 60 °C

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

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

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

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