(3R,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-cyclohexa-1,5-dienecarboxylic acid methyl ester

Base Information

Chemical Name:(3R,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-cyclohexa-1,5-dienecarboxylic acid methyl ester
CAS No.:97279-83-9
Molecular Formula:C₁₃H₁₉NO₅
Molecular Weight:269.298
Hs Code.:

Synonyms:(3R,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-cyclohexa-1,5-dienecarboxylic acid methyl ester

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Chemical Property of (3R,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-cyclohexa-1,5-dienecarboxylic acid methyl ester

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Technology Process of (3R,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-cyclohexa-1,5-dienecarboxylic acid methyl ester

There total 1 articles about (3R,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-cyclohexa-1,5-dienecarboxylic acid methyl 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:

: 97279-81-7
trans-4-amino-3-hydroxy-1,5-cyclohexadiene-1-carboxylic acid

: 74-88-4
methyl iodide

: 97279-83-9
(3R,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-cyclohexa-1,5-dienecarboxylic acid methyl ester

Guidance literature:: With sodium hydrogencarbonate; Yield given. Multistep reaction; 2.) HMPA;
DOI:10.1021/ja00303a038

Reference yield: 56.0%

: 2-Diazenyl-malonic acid dimethyl ester

: 97279-83-9
(3R,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-cyclohexa-1,5-dienecarboxylic acid methyl ester

: 97279-84-0
2-((1S,6S)-6-tert-Butoxycarbonylamino-3-methoxycarbonyl-cyclohexa-2,4-dienyloxy)-malonic acid dimethyl ester

Guidance literature:: With dirhodium tetraacetate; In benzene; at 70 ℃;
DOI:10.1021/ja00303a038

Reference yield:

: 97279-83-9
(3R,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-cyclohexa-1,5-dienecarboxylic acid methyl ester

: 150-13-0,159246-81-8,8014-65-1
4-amino-benzoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 56 percent / Rh₂(OAc)4 / benzene / 70 °C

2: 94 percent / Et₃N / CH₂Cl₂ / Ambient temperature

3: CH₂Cl₂ / Ambient temperature

4: 47 percent / NaOH / tetrahydrofuran; H₂O

5: NaOH

6: 68 percent / tetrahydrofuran / 0.25 h / 0 °C

7: plasmid-containing strain of E coli BN 116, NH₄⁽¹⁺⁾

With dirhodium tetraacetate; sodium hydroxide; ammonium; plasmid-containing strain of E coli BN 116; triethylamine; In tetrahydrofuran; dichloromethane; water; benzene;
DOI:10.1021/ja00303a038