(1R,2R,3S,4S)-3-(tert-Butoxycarbonylamino)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Base Information

• Chemical Name: (1R,2R,3S,4S)-3-(tert-Butoxycarbonylamino)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• CAS No.: 871357-91-4
• Molecular Formula: C₁₃H₁₉NO₄
• Molecular Weight: 253.298
• Hs Code.: 2924297099
• Mol file: 871357-91-4.mol

Synonyms:(1R,2R,3S,4S)-3-exo-N-^tbutyloxycarbonylaminobicyclo[2,2,1]hept-5-ene-2-exo-carboxylic acid

Chemical Property of (1R,2R,3S,4S)-3-(tert-Butoxycarbonylamino)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

(1R,2R,3S,4S)-3-(tert-Butoxycarbonylamino)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4S)-3-(tert-Butoxycarbonylamino)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

There total 12 articles about (1R,2R,3S,4S)-3-(tert-Butoxycarbonylamino)bicyclo[2.2.1]hept-5-ene-2-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: 87.0%

di-tert-butyl dicarbonate (24424-99-5) + (1R,2R,3S,4S)-3-exo-aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (202187-27-7,202187-24-4,202187-28-8,202187-29-9) → (1R,2R,3S,4S)-3-exo-N-tbutyloxycarbonylaminobicyclo[2,2,1]hept-5-ene-2-exo-carboxylic acid (871357-91-4,1242184-48-0,1242184-46-8,148257-06-1)

Guidance literature:

With water; sodium hydroxide; In 1,4-dioxane; at 0 - 20 ℃;

DOI:10.3390/molecules24040772

Reference yield: 48.0%

(1SR,2SR,5RS,6RS)-4-oxo-3-aza-tricyclo[4.2.1.0(2,5)]non-7-ene-3-carboxylic acid tert-butyl ester (871357-90-3) → (1R,2R,3S,4S)-3-exo-N-tbutyloxycarbonylaminobicyclo[2,2,1]hept-5-ene-2-exo-carboxylic acid (871357-91-4,1242184-48-0,1242184-46-8,148257-06-1) + ((1R,2R,3S,4S)-3-carbamoyl-bicyclo[2.2.1]hept-5-en-2-yl)-carbamic acid tert-butyl ester (871357-92-5)

Guidance literature:

(1SR,2SR,5RS,6RS)-4-oxo-3-aza-tricyclo[4.2.1.0(2,5)]non-7-ene-3-carboxylic acid tert-butyl ester; In tert-butyl methyl ether; water; at 50 ℃; for 144h; Large scale reaction; Enzymatic reaction;

With ammonium hydroxide; In tert-butyl methyl ether; water; at 30 - 34 ℃; for 18h; optical yield given as %ee; enantioselective reaction; Large scale reaction;

DOI:10.1021/op200313v

Reference yield:

ethyl (1R,2R,3S,4S)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate (790187-08-5) → (1R,2R,3S,4S)-3-exo-N-tbutyloxycarbonylaminobicyclo[2,2,1]hept-5-ene-2-exo-carboxylic acid (871357-91-4,1242184-48-0,1242184-46-8,148257-06-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; water / 0.5 h / 100 °C / Microwave irradiation

2: sodium hydroxide; water / 1,4-dioxane / 0 - 20 °C

With water; sodium hydroxide; In 1,4-dioxane;

DOI:10.3390/molecules24040772

upstream raw materials:

di-tert-butyl dicarbonate

(1R,2R,3S,4S)-3-exo-aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid

(1SR,2SR,5RS,6RS)-4-oxo-3-aza-tricyclo[4.2.1.0(2,5)]non-7-ene-3-carboxylic acid tert-butyl ester

diexo-3-Aza-4-oxotricyclo<4.2.1.0^2,5>non-7-ene

Refernces

• 1、 -. "Mediators of hedgehog signaling pathways, compositions and uses related thereto". Page/Page column 77; 78. . Retrieved 2015/11/27.
• 2、 Chandrasekhar, Srivari,Babu, Bathini Nagendra,Prabhakar, Anabathula,Sudhakar, Ambadi,Reddy, Marepally Srinivasa,Kiran, Marelli Udaya,Jagadeesh, Bharatam. "Oligomers of cis-β-norbornene amino acid: Formation of β-strand mimetics". . p. 1548 - 1550. Retrieved 2008/03/12.