tert-butyl(2'S,5S,6S)-(+)-2'-[6-tert-butoxycarbonylamino-5-hydroxycyclohexa-1,3-diene-1-carbonyloxy]propionate

Base Information

Chemical Name:tert-butyl(2'S,5S,6S)-(+)-2'-[6-tert-butoxycarbonylamino-5-hydroxycyclohexa-1,3-diene-1-carbonyloxy]propionate
CAS No.:501085-42-3
Molecular Formula:C₁₉H₂₉NO₇
Molecular Weight:383.442
Hs Code.:

Synonyms:tert-butyl(2'S,5S,6S)-(+)-2'-[6-tert-butoxycarbonylamino-5-hydroxycyclohexa-1,3-diene-1-carbonyloxy]propionate

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Chemical Property of tert-butyl(2'S,5S,6S)-(+)-2'-[6-tert-butoxycarbonylamino-5-hydroxycyclohexa-1,3-diene-1-carbonyloxy]propionate

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Technology Process of tert-butyl(2'S,5S,6S)-(+)-2'-[6-tert-butoxycarbonylamino-5-hydroxycyclohexa-1,3-diene-1-carbonyloxy]propionate

There total 4 articles about tert-butyl(2'S,5S,6S)-(+)-2'-[6-tert-butoxycarbonylamino-5-hydroxycyclohexa-1,3-diene-1-carbonyloxy]propionate 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: 89.0%

: 89557-24-4
(5S,6S)-6-tert-Butoxycarbonylamino-5-hydroxy-cyclohexa-1,3-dienecarboxylic acid

: 2-methanesulfonyloxy-propionic acid tert-butyl ester

: 501085-42-3
tert-butyl(2'S,5S,6S)-(+)-2'-[6-tert-butoxycarbonylamino-5-hydroxycyclohexa-1,3-diene-1-carbonyloxy]propionate

Guidance literature:: (5S,6S)-6-tert-Butoxycarbonylamino-5-hydroxy-cyclohexa-1,3-dienecarboxylic acid; With cesium fluoride; In N,N-dimethyl-formamide; at 25 ℃; for 0.5h;

2-methanesulfonyloxy-propionic acid tert-butyl ester; at 50 ℃; for 24h; Further stages.;
DOI:10.1021/ol0269704

Reference yield:

: 84751-41-7,89299-58-1,89299-59-2
ethyl (1SR,2RS,3RS,4RS)-3-nitro-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate

: 501085-42-3
tert-butyl(2'S,5S,6S)-(+)-2'-[6-tert-butoxycarbonylamino-5-hydroxycyclohexa-1,3-diene-1-carbonyloxy]propionate

Guidance literature:: Multi-step reaction with 4 steps

1.1: zinc; HCl / ethanol

1.2: diisopropylethylamine

2.1: potassium hexamethyldisilazide / tetrahydrofuran / -50 - 25 °C

3.1: potassium hydroxide / tetrahydrofuran; H₂O

4.1: CsF / dimethylformamide / 0.5 h / 25 °C

4.2: 89 percent / 24 h / 50 °C

With hydrogenchloride; potassium hydroxide; potassium hexamethylsilazane; cesium fluoride; zinc; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0269704

Reference yield:

: 501085-40-1
rac-ethyl trans-6-[(tert-butoxycarbonyl)amino]-5-hydroxycyclohexa-1,3-diene-1-carboxylate

: 501085-42-3
tert-butyl(2'S,5S,6S)-(+)-2'-[6-tert-butoxycarbonylamino-5-hydroxycyclohexa-1,3-diene-1-carbonyloxy]propionate

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hydroxide / tetrahydrofuran; H₂O

2.1: CsF / dimethylformamide / 0.5 h / 25 °C

2.2: 89 percent / 24 h / 50 °C

With potassium hydroxide; cesium fluoride; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0269704