ethyl (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate

Base Information

Chemical Name:ethyl (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate
CAS No.:1428733-29-2
Molecular Formula:C₁₄H₂₃NO₅
Molecular Weight:285.34
Hs Code.:

Synonyms:ethyl (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate

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Chemical Property of ethyl (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate

Chemical Property:

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Technology Process of ethyl (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate

There total 12 articles about ethyl (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-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:

: 1428733-30-5
(4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylic acid

: 75-03-6
ethyl iodide

: 1428733-29-2
ethyl (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate

Guidance literature:: (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylic acid; With potassium carbonate; In ethanol; water; at 20 ℃; for 0.5h;

ethyl iodide; In dimethyl sulfoxide; at 20 ℃; for 40h;
DOI:10.1055/s-0032-1317948

Reference yield:

: 53100-44-0,160347-90-0
L-N-t-butoxycarbonylpyroglutamic acid

: 1428733-29-2
ethyl (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 11 steps

1.1: isobutyl chloroformate; triethylamine / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

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

2.1: triethylsilane; palladium 10% on activated carbon / acetone / 0.75 h / 20 °C / Inert atmosphere

3.1: indium / tetrahydrofuran; water / 16 h

4.1: sodium tetrahydroborate / tetrahydrofuran; water / 18 h / 20 °C

5.1: toluene-4-sulfonic acid / dichloromethane / 0.75 h / 20 °C

6.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

7.1: triethylamine / dichloromethane / 18 h / 20 °C

8.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / 35 °C / Inert atmosphere

9.1: lithium chloride / water; acetic acid / 1 h / 20 °C

10.1: Oxone / N,N-dimethyl-formamide / 4.5 h / 20 °C

11.1: potassium carbonate / water; ethanol / 0.5 h / 20 °C

11.2: 40 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triethylsilane; Oxone; indium; sodium tetrahydroborate; palladium 10% on activated carbon; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; lithium chloride; isobutyl chloroformate; In tetrahydrofuran; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;
DOI:10.1055/s-0032-1317948

Reference yield:

: 185303-87-1
tert-butyl (S)-2-formyl-5-oxopyrrolidine-1-carboxylate

: 1428733-29-2
ethyl (4R,5S)-5-(tert-butoxycarbonylamino)-4-hydroxycyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: indium / tetrahydrofuran; water / 16 h

2.1: sodium tetrahydroborate / tetrahydrofuran; water / 18 h / 20 °C

3.1: toluene-4-sulfonic acid / dichloromethane / 0.75 h / 20 °C

4.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

5.1: propionic acid; pyrrolidine / isopropyl alcohol / 18 h / 20 °C

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / 35 °C / Inert atmosphere

7.1: lithium chloride / water; acetic acid / 1 h / 20 °C

8.1: Oxone / N,N-dimethyl-formamide / 4.5 h / 20 °C

9.1: potassium carbonate / water; ethanol / 0.5 h / 20 °C

9.2: 40 h / 20 °C

With pyrrolidine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; Oxone; indium; sodium tetrahydroborate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; propionic acid; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1055/s-0032-1317948