168960-18-7

Basic information

• Product Name: Carbamic acid, [(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester
• Synonyms: TERT-BUTYL CIS-[4(S)-(HYDROXYMETHYL)CYCLOPENT-2-EN-1(R)-YL]CARBAMATE; Carbamic acid, [(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-, 1,1-; TERT-BUTYL (1R,4S)-4-(HYDROXYMETHYL)CYCLOPENT-2-ENYLCARBAMATE
• CAS NO: 168960-18-7
• Molecular Formula: C₁₁H₁₉NO₃
• Molecular Weight: 213.27
• Product Categories: N-BOC
• Mol File: 168960-18-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 338.8±31.0 °C(Predicted)
• Appearance: /
• Density: 1.09±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: DMSO; Methanol
• PKA: 12.06±0.40(Predicted)
• CAS DataBase Reference: Carbamic acid, [(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester(168960-18-7)
• EPA Substance Registry System: Carbamic acid, [(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-, 1,1-dimethylethyl ester(168960-18-7)

Safety Data

• Hazardous Substances Data: 168960-18-7(Hazardous Substances Data)

Usage

Uses

N-?[(1R,?4S)?-?4-?(Hydroxymethyl)?-?2-?cyclopenten-?1-?yl]?-carbamic Acid 1,?1-?Dimethylethyl Ester is an intermediate in synthesizing ent-Abacavir (Abacavir EP Impurity A) (A105015), an enatiomer of Abacavir (A105000). Abacavir is a carbocyclic 2''-deoxyguanosine nucleoside reverse transcriptase inhibitor and an anti-HIV drug used to treat HIV infection (1). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (2). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 136522-35-5 (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene 
• 419563-22-7 (1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester tartrate 
• 49805-30-3 racemic 2-azabicyclo[2.2.1]hept-5-en-3-one 
• 151907-79-8 (1S-cis)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid 
• 34619-03-9 tert-butyldicarbonate 
• 168960-17-6 (1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one 
• 168773-36-2 (5S,6R)-5-Hydroxy-6-<(benzyloxy)methyl>-2-piperidinone 
• 168773-68-0 (1R,2S,4S)-1-<(tert-Butyloxycarbonyl)amino>-2-<<(p-methylphenoxy)thiocarbonyl>oxy>-4-<(methoxymethoxy)methyl>cyclopentane 
• 168773-43-1 (5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone 
• 168773-58-8 Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester 
• 168773-66-8 Imidazole-1-carbothioic acid O-((1S,2R,4S)-2-tert-butoxycarbonylamino-4-methoxymethoxymethyl-cyclopentyl) ester 
• 168773-40-8 (5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone 
• 173464-46-5 (1S,4R)-4-Azido-1-benzoyloxycyclopent-2-ene 

Downstream Products

• 136522-35-5 (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene 
• 141271-12-7 (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol 
• 859147-56-1 N-1-[(1R,4S)-4-{(monomethoxytrityl)oxymethyl}cyclopent-2-en-1-yl]-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine 
• 859147-52-7 N-1-[(1R,4S)-4-{(monomethoxytrityl)oxymethyl}cyclopent-2-en-1-yl]-5',O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneadenosine 
• 859147-54-9 N-1-[(1R,4S)-4-{(monomethoxytrityl)oxymethyl}cyclopent-2-en-1-yl]-2',3'-O-isopropylideneadenosine 
• 859147-58-3 N-1-{(1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl}-5,-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine 
• 112966-73-1 [(1R,3S)-3-(6-amino-9H-purin-9-yl)cyclopentyl]methanol 
• 918492-98-5 (1α,4α)-4-(6-Chloro-9H-purin-9-yl)-2-cyclopentenyl-carbinol 
• 168960-19-8 (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride 

Relevant articles and documents

Optical pure amino alcohol hydrochloride preparation method

The invention relates to a preparation method for optically pure aminoalcohol hydrochloride. The optically pure aminoalcohol hydrochloride is any one selected from optically pure aminoalcohol hydrochloride 1 and optically pure aminoalcohol hydrochloride 2 and is prepared by subjecting a compound 4 to an esterification ring-opening reaction, an amino protection reaction, an ester reduction reaction and a deprotection salt forming reaction. The optically pure aminoalcohol hydrochloride 1 or optically pure aminoalcohol hydrochloride 2 prepared in the invention can be directly used for synthesis of abacavir and carbovir. The preparation method provided by the invention has the advantages of high product optical purity, stable product quality, high product yield, a small amount of environmental pollution, low production cost, easy industrialization, etc.

Application of phosphoramidate ProTide technology significantly improves antiviral potency of carbocyclic adenosine derivatives

We report the application of phosphoramidate pronucleotide (ProTide) technology to the antiviral agent carbocyclic L-d4A (L-Cd4A). The phenyl methyl alaninyl parent ProTide of L-Cd4A was prepared by Grignard-mediated phosphorochloridate reaction and resulted in a compound with significantly improved anti-HIV (2600-fold) and HBV activity. We describe modifications of the aryl, ester, and amino acid regions of the ProTide and how these changes affect antiviral activity and metabolic stability. Separate and distinct SARs were noted for HIV and HBV. Additionally, ProTides were prepared from the D-nucleoside D-Cd4A and the dideoxy analogues L-CddA and D-CddA. These compounds showed more modest potency improvements over the parent drug. In conclusion, the ProTide approach is highly successful when applied to L-Cd4A with potency improvements in vitro as high as 9000-fold against HIV. With a view to preclinical candidate selection we carried out metabolic stability studies using cynomolgus monkey liver and intestinal S9 fractions.

Therapeutic nucleosides

The present invention relates to intermediates useful for the preparation of certain compounds, for example, purine carbocyclic nucleosides.