(5R,6R)-6-tert-Butoxycarbonylamino-5-hydroxy-cyclohexa-1,3-dienecarboxylic acid ethyl ester

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Chemical Name:(5R,6R)-6-tert-Butoxycarbonylamino-5-hydroxy-cyclohexa-1,3-dienecarboxylic acid ethyl ester
CAS No.:501085-47-8
Molecular Formula:C₁₄H₂₁NO₅
Molecular Weight:283.324
Hs Code.:

Synonyms:(5R,6R)-6-tert-Butoxycarbonylamino-5-hydroxy-cyclohexa-1,3-dienecarboxylic acid ethyl ester

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Chemical Property of (5R,6R)-6-tert-Butoxycarbonylamino-5-hydroxy-cyclohexa-1,3-dienecarboxylic acid ethyl ester

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Technology Process of (5R,6R)-6-tert-Butoxycarbonylamino-5-hydroxy-cyclohexa-1,3-dienecarboxylic acid ethyl ester

There total 5 articles about (5R,6R)-6-tert-Butoxycarbonylamino-5-hydroxy-cyclohexa-1,3-dienecarboxylic acid ethyl ester 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%

: 501085-45-6
(1S,2R,3R,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester

: 7781-98-8
ethyl-3-hydroxybenzoate

: 501085-47-8
(5R,6R)-6-tert-Butoxycarbonylamino-5-hydroxy-cyclohexa-1,3-dienecarboxylic acid ethyl ester

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; at -50 - 25 ℃;
DOI:10.1021/ol0269704

Reference yield:

: 5941-50-4,1851-82-7,105576-14-5
(E)-ethyl 3-nitroacrylate

: 501085-47-8
(5R,6R)-6-tert-Butoxycarbonylamino-5-hydroxy-cyclohexa-1,3-dienecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: CHCl₃ / 120 h / -20 °C

2.1: zinc; HCl / ethanol

2.2: diisopropylethylamine

3.1: 71 percent / potassium hexamethyldisilazide / tetrahydrofuran / -50 - 25 °C

With hydrogenchloride; potassium hexamethylsilazane; zinc; In tetrahydrofuran; ethanol; chloroform; 1.1: Diels-Alder reaction;
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

: 501085-47-8
(5R,6R)-6-tert-Butoxycarbonylamino-5-hydroxy-cyclohexa-1,3-dienecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: zinc; HCl / ethanol

1.2: diisopropylethylamine

2.1: 71 percent / potassium hexamethyldisilazide / tetrahydrofuran / -50 - 25 °C

With hydrogenchloride; potassium hexamethylsilazane; zinc; In tetrahydrofuran; ethanol;
DOI:10.1021/ol0269704