(3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid

Base Information

• Chemical Name: (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid
• CAS No.: 506444-80-0
• Molecular Formula: C₁₇H₁₉NO₆
• Molecular Weight: 333.341
• Mol file: 506444-80-0.mol

Synonyms:(3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid

Chemical Property of (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid

There total 3 articles about (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid 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:

(3'S,4'S,4S)-3'-(N'-p-methoxycarbonylbenzyloxycarbonylamino-1'-cyclohexene-4'-carbonyl)-[4-tert-butyl-2'-oxazolidinone] (506444-78-6) → (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid (506444-80-0)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 22 ℃; for 2h;

DOI:10.1021/ja020879d

Reference yield:

4-(methoxycarbonyl)benzyl alcohol (6908-41-4,58590-49-1) → (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid (506444-80-0)

Guidance literature:

Multi-step reaction with 3 steps

1: catechol / toluene / 0.5 h / Heating

2: 1,2-dihydroxy-4-(tert-butyl)benzene / benzene / 72 h / Heating

3: aq. hydrogen peroxide; LiOH / tetrahydrofuran / 2 h / 22 °C

With lithium hydroxide; 4-tert-Butylcatechol; dihydrogen peroxide; benzene-1,2-diol; In tetrahydrofuran; toluene; benzene; 2: Diels-Alder reaction;

DOI:10.1021/ja020879d

Reference yield:

4-(methoxycarbonyl)benzyl trans-1,3-butadiene-1-carbamate (152839-68-4) → (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid (506444-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,2-dihydroxy-4-(tert-butyl)benzene / benzene / 72 h / Heating

2: aq. hydrogen peroxide; LiOH / tetrahydrofuran / 2 h / 22 °C

With lithium hydroxide; 4-tert-Butylcatechol; dihydrogen peroxide; In tetrahydrofuran; benzene; 1: Diels-Alder reaction;

DOI:10.1021/ja020879d

upstream raw materials:

(3'S,4'S,4S)-3'-(N'-p-methoxycarbonylbenzyloxycarbonylamino-1'-cyclohexene-4'-carbonyl)-[4-tert-butyl-2'-oxazolidinone]

4-(methoxycarbonyl)benzyl alcohol

4-(methoxycarbonyl)benzyl trans-1,3-butadiene-1-carbamate

Downstream raw materials:

(3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-N,N-dimethylcarboxamide

rac-trans-2-aminocyclohexanecarboxylic acid