ehyl (3R,4S,5S,6R)-4-acetamido-6-hydroxy-3-(pent-3-yloxy)-5-(tosyloxy)cyclohex-1-enecarboxylate

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Chemical Name:ehyl (3R,4S,5S,6R)-4-acetamido-6-hydroxy-3-(pent-3-yloxy)-5-(tosyloxy)cyclohex-1-enecarboxylate
CAS No.:1196490-09-1
Molecular Formula:C₂₃H₃₃NO₈S
Molecular Weight:483.583
Hs Code.:

Synonyms:ehyl (3R,4S,5S,6R)-4-acetamido-6-hydroxy-3-(pent-3-yloxy)-5-(tosyloxy)cyclohex-1-enecarboxylate

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Chemical Property of ehyl (3R,4S,5S,6R)-4-acetamido-6-hydroxy-3-(pent-3-yloxy)-5-(tosyloxy)cyclohex-1-enecarboxylate

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Technology Process of ehyl (3R,4S,5S,6R)-4-acetamido-6-hydroxy-3-(pent-3-yloxy)-5-(tosyloxy)cyclohex-1-enecarboxylate

There total 7 articles about ehyl (3R,4S,5S,6R)-4-acetamido-6-hydroxy-3-(pent-3-yloxy)-5-(tosyloxy)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: 76.0%

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

: 98-59-9
p-toluenesulfonyl chloride

: 1196490-09-1
ehyl (3R,4S,5S,6R)-4-acetamido-6-hydroxy-3-(pent-3-yloxy)-5-(tosyloxy)cyclohex-1-enecarboxylate

Guidance literature:: With pyridine; at 20 ℃; for 48.0833h;

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

: 1196490-09-1
ehyl (3R,4S,5S,6R)-4-acetamido-6-hydroxy-3-(pent-3-yloxy)-5-(tosyloxy)cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 4 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

With pyridine; hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(II) bis(trifluoromethanesulfonate); triethylamine; In ethanol; 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

: 1196490-09-1
ehyl (3R,4S,5S,6R)-4-acetamido-6-hydroxy-3-(pent-3-yloxy)-5-(tosyloxy)cyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 5 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

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