189625-14-7

Basic information

• Product Name: Carbamic acid, [(1R,4S)-4-(acetyloxy)-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester
• Synonyms: (-)-cis-N-(tert-butoxycarbonyl)-4-aminocyclopent-2-enol-1-O-acetate;Acetic acid (1S,4R)-4-tert-butoxycarbonylamino-cyclopent-2-enyl ester
• CAS NO: 189625-14-7
• Molecular Formula: C12H19NO4
• Molecular Weight: 241.28400
• Mol File: 189625-14-7.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(1R,4S)-4-(acetyloxy)-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1R,4S)-4-(acetyloxy)-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester(189625-14-7)
• EPA Substance Registry System: Carbamic acid, [(1R,4S)-4-(acetyloxy)-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester(189625-14-7)

Safety Data

• Hazardous Substances Data: 189625-14-7(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 108-24-7 acetic anhydride 
• 220354-28-9 [1S-cis]-4-amino-2-cyclopenten-1-ol 
• 108-05-4 vinyl acetate 
• 657396-96-8 (4-hydroxycyclopent-2-enyl)-carbamic acid tert-butyl ester 
• 154802-92-3 (+/-)-1-hydroxy-4-[(tert-butoxycarbonyl)amino]-2-cyclopentene 
• 75-36-5 acetyl chloride 
• 189625-12-5 (+)-(1S,4R)-1-hydroxy-4-[(tert-butoxycarbonyl)amino]-2-cyclopentene 
• 201054-55-9 (+)-(1R,4S)-1-hydroxy-4-[(tert-butoxycarbonyl)amino]-2-cyclopentene 
• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 542-92-7 cyclopenta-1,3-diene 
• 99027-90-4 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylic acidtert-butyl ester 
• 154802-92-3 tert-butyl cis-N-[4-hydroxycyclopent-2-en-1-yl]carbamate 
• 171754-76-0 Acetic acid (1S,4R)-4-((R)-2-tert-butoxycarbonylamino-propionylamino)-cyclopent-2-enyl ester 

Downstream Products

• 225641-82-7 Acetic acid (1R,3S)-3-tert-butoxycarbonylamino-cyclopentyl ester 
• 167465-99-8 (1S,3R)-3-hydroxycyclopentyl-1-carbamic acid tert-butyl ester 
• 1233220-23-9 (+)-tert-butyl (1R,4R)-4-(hydroxymethyl)cyclopent-2-enylcarbamate 
• 1233220-24-0 (+)-tert-butyl (1R,4R)-2-(hydroxymethyl)cyclopent-3-enylcarbamate 
• 657397-01-8 (2R)-(4-oxocyclopent-2-enyl)-carbamic acid tert-butyl ester 
• 725233-49-8 (-)-1-{(1'R,2'S,3'R,4'S)-4'-[(R)-methoxycarbonyl(benzyloxycarbonylamino)methyl]-2',3'-dihydroxycyclopentyl}uracil 
• 725233-48-7 (-)-1-{(1'R,2'S,3'R,4'S)-4'-[(S)-methoxycarbonyl(benzyloxycarbonylamino)methyl]-2',3'-dihydroxycyclopentyl}uracil 
• 725233-47-6 (-)-1-{(1'R,4'S)-4'-[(R)-methoxycarbonyl(benzyloxycarbonylamino)methyl]cyclopent-2'-enyl}uracil 
• 725233-46-5 (-)-1-{(1'R,4'S)-4'-[(S)-methoxycarbonyl(benzyloxycarbonylamino)methyl]cyclopent-2'-enyl}uracil 
• 725233-44-3 (-)-(3R,5S)-3-(tert-butoxycarbonylamino)-5-[(R)-methoxycarbonyl(benzyloxycarbonylamino)methyl]cyclpent-1-ene 
• 725233-43-2 (-)-(3R,5S)-3-(tert-butoxycarbonylamino)-5-[(S)-methoxycarbonyl(benzyloxycarbonylamino)methyl]cyclpent-1-ene 
• 189625-12-5 (+)-(1S,4R)-1-hydroxy-4-[(tert-butoxycarbonyl)amino]-2-cyclopentene 

Relevant articles and documents

Method for preparing (1R, 3S)-3-aminocyclopentanol hydrochloride

The invention discloses a method for preparing (1R, 3S) 3-aminocyclopentanol hydrochloride, belongs to the field of organic chemical synthesis, and provides a process route to overcome the defects ofhigh price, difficulty in chiral control and the like in the prior art. The process route comprises the following steps: 1) oxidizing tert-butyl carbonate hydroxylamine into tert-butyl carbonate nitrosyl under the catalysis of copper chloride and 2-ethyl-2-oxazoline, then carrying out a hetero Diels-Alder reaction with cyclopentadiene in situ; 2) selectively reducing nitrogen-oxygen bonds in a zinc powder-acetic acid reaction system; 3) under the catalysis of lipase, reacting with vinyl acetate to optically and selectively realize chiral resolution; 4) reducing double bonds through palladium carbon hydrogenation; 5) under the alkaline condition of lithium hydroxide-methanol, performing deacetylation protection; and 6) removing tert-butyl carbonate protection in a hydrogen chloride isopropanol acid solution prepared from acetyl chloride and isopropanol in situ, and forming hydrochloride in situ to obtain a target product. The synthetic method has the beneficial effects that the synthetic method has the characteristics of novel and short route, high optical purity, low cost and the like.

Total synthesis of (-)-agelastatin A

(Chemical Equation Presented) A new route to (-)-agelastatin A is reported. The requisite nitrogen functionalities of the agelastatin core have been installed by intramolecular aziridination of an azidoformate and subsequent regioselective azidation, lead

Chemoenzymatic asymmetric total synthesis of phosphodiesterase inhibitors: Preparation of a polycyclic pyrazolo[3,4-d]pyrimidine from an acylnitroso Diels-Alder cycloadduct-derived aminocyclopentenol

(Chemical Equation Presented) Enzymatic resolution of Boc-protected 4-aminocyclopenten1-ol 4c gave both enantiomers 5c and 6c in high ee. Boc removal and separate condensation with chloropyrazolopyrimidine 18 provided elaborated 1,4-aminocyclopentenol derivatives 20 and 26, respectively. Separate treatment of 20 and 26 with Pd(0) under basic conditions induced cyclization to unsaturated polycycles 22 and 27, which, upon catalytic hydrogenation, were transformed to new cyclopentane-containing pyrazolopyrimidines 24 and 28, analogues of recently described novel phosphodiesterase inhibitors.