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

Base Information

• Chemical Name: (1S,2R,3R,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester
• CAS No.: 501085-45-6
• Molecular Formula: C₁₄H₂₁NO₅
• Molecular Weight: 283.324
• Mol file: 501085-45-6.mol

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

Chemical Property of (1S,2R,3R,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3R,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester

There total 2 articles about (1S,2R,3R,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic 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: 48.0%

rac-ethyl endo-3-[(tert-butoxycarbonyl)amino]-7-oxabicyclo[2.2.1]hept-5-ene-exo-2-carboxylate → (1R,2S,3S,4S)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid + (1S,2R,3R,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester (501085-45-6)

Guidance literature:

With phosphate buffer; PLE enzyme; In diethyl ether; at 20 ℃; for 96h; pH=8;

DOI:10.1021/ol0269704

Reference yield:

rac-ethyl endo-3-[(tert-butoxycarbonyl)amino]-7-oxabicyclo[2.2.1]hept-5-ene-exo-2-carboxylate → C12H17NO5 + (1R,2S,3S,4S)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid + (1R,2S,3S,4S)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester (501085-41-2) + (1S,2R,3R,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester (501085-45-6)

Guidance literature:

With horse liver powder acetone, HLPA; at 20 ℃; for 23h; optical yield given as %ee; Resolution of racemate; TRIS buffer; Enzymatic reaction;

DOI:10.1039/c2ob25060h

Reference yield: 71.0%

(1S,2R,3R,4R)-3-tert-Butoxycarbonylamino-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester (501085-45-6) → ethyl-3-hydroxybenzoate (7781-98-8) + (5R,6R)-6-tert-Butoxycarbonylamino-5-hydroxy-cyclohexa-1,3-dienecarboxylic acid ethyl ester (501085-47-8)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -50 - 25 ℃;

DOI:10.1021/ol0269704

Downstream raw materials:

ethyl-3-hydroxybenzoate

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

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

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