(1S,4R)-Acetic acid 4-tert-butoxycarbonylamino-cyclopent-2-enyl ester

Base Information

• Chemical Name: (1S,4R)-Acetic acid 4-tert-butoxycarbonylamino-cyclopent-2-enyl ester
• CAS No.: 189625-14-7
• Molecular Formula: C12H19NO4
• Molecular Weight: 241.28400
• DSSTox Substance ID: DTXSID001151997
• Nikkaji Number: J966.242A
• Mol file: 189625-14-7.mol

Synonyms:189625-14-7;(1S,4R)-Acetic acid 4-tert-butoxycarbonylamino-cyclopent-2-enyl ester;[(1S,4R)-4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopent-2-en-1-yl] acetate;SCHEMBL13749336;DTXSID001151997;MFCD20278271;CS-0340324;3beta-Acetoxy-5beta-(tert-butoxycarbonylamino)cyclopentene;(1S,4R)-Acetic acid 4-t-butoxycarbonylamino-cyclopent-2-enyl ester;(1S,4R)-Aceticacid4-tert-butoxycarbonylamino-cyclopent-2-enylester;1,1-Dimethylethyl N-[(1R,4S)-4-(acetyloxy)-2-cyclopenten-1-yl]carbamate

Chemical Property of (1S,4R)-Acetic acid 4-tert-butoxycarbonylamino-cyclopent-2-enyl ester

Chemical Property:

• PSA: 64.63000
• LogP: 2.16220
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 241.13140809
• Heavy Atom Count: 17
• Complexity: 330

Purity/Quality:

98% ^*data from raw suppliers

(1S,4R)-Aceticacid4-tert-butoxycarbonylamino-cyclopent-2-enylester 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CC(C=C1)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(=O)O[C@H]1C[C@H](C=C1)NC(=O)OC(C)(C)C

Technology Process of (1S,4R)-Acetic acid 4-tert-butoxycarbonylamino-cyclopent-2-enyl ester

There total 23 articles about (1S,4R)-Acetic acid 4-tert-butoxycarbonylamino-cyclopent-2-enyl 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: 100.0%

acetyl chloride (75-36-5) + (+)-(1S,4R)-1-hydroxy-4-[(tert-butoxycarbonyl)amino]-2-cyclopentene (189625-12-5,154802-92-3,178152-48-2) → (2S,4R)-acetic acid 4-tert-butoxycarbonylaminocyclopent-2-enyl ester (189625-14-7)

Guidance literature:

In pyridine; dichloromethane; at 0 ℃;

DOI:10.1021/jo971711r

Reference yield: 48.0%

vinyl acetate (108-05-4,9003-20-7) + (+/-)-1-hydroxy-4-[(tert-butoxycarbonyl)amino]-2-cyclopentene (154802-92-3,178152-48-2) → (2S,4R)-acetic acid 4-tert-butoxycarbonylaminocyclopent-2-enyl ester (189625-14-7) + (+)-(1R,4S)-1-hydroxy-4-[(tert-butoxycarbonyl)amino]-2-cyclopentene (201054-55-9,154802-92-3,178152-48-2)

Guidance literature:

With lipase PS-C Amano II; In dichloromethane; at 20 ℃; for 50h; optical yield given as %ee; Enzymatic reaction;

DOI:10.1021/ol802225g

Reference yield: 43.0%

vinyl acetate (108-05-4,9003-20-7) + tert-butyl cis-N-[4-hydroxycyclopent-2-en-1-yl]carbamate (154802-92-3,178152-48-2) → (2S,4R)-acetic acid 4-tert-butoxycarbonylaminocyclopent-2-enyl ester (189625-14-7)

Guidance literature:

With Lipase PS "Amano" SD; In dichloromethane; at 25 ℃; for 72h; Reagent/catalyst;

upstream raw materials:

di-tert-butyl dicarbonate

Isopropenyl acetate

(+/-)-1-hydroxy-4-[(tert-butoxycarbonyl)amino]-2-cyclopentene

acetic anhydride

Downstream raw materials:

Acetic acid (1R,3S)-3-tert-butoxycarbonylamino-cyclopentyl ester

(1S,3R)-3-hydroxycyclopentyl-1-carbamic acid tert-butyl ester

(2R)-(4-oxocyclopent-2-enyl)-carbamic acid tert-butyl ester

(-)-1-{(1'R,2'S,3'R,4'S)-4'-[(R)-methoxycarbonyl(benzyloxycarbonylamino)methyl]-2',3'-dihydroxycyclopentyl}uracil

Refernces

• 1、 Tardibono Jr., Lawrence P.,Miller, Marvin J.,Balzarini, Jan. "Enantioselective syntheses of carbocyclic nucleosides 5′- homocarbovir, epi-4′-homocarbovir, and their cyclopropylamine analogs using facially selective Pd-mediated allylations". scheme or table. p. 825 - 829. Retrieved 2011/03/19.
• 2、 Huang, Weiqiang,Miller, Marvin J.. "Concise syntheses of enantiomerically pure protected 4-hydroxypyroglutamic acid and 4-hydroxyproline from a nitroso-cyclopentadiene cycloadduct". experimental part. p. 2835 - 2838. Retrieved 2009/06/28.