168960-19-8Relevant academic research and scientific papers
A facile synthesis of cis-4-amino-2-cyclopentene-1-methanol, a key intermediate for the synthesis of carbocyclic nucleosides
An, Gwang-Il,Rhee, Hakjune
, p. 65 - 72 (2002)
A number of carbocyclic nucleosides can be synthesized from (±)-cis-4-amino-2-cyclopentene-1-methanol (3). Carbocyclic amino alcohol 3 is a key intermediate that makes possible the efficient synthesis of the carbocyclic nucleosides. In this study we wish to report an efficient synthesis of carbocyclic amino alcohol 3 from inexpensive and readily available starting material. The synthetic route employed cyclopentadiene (4) as a starting material and proceeded in 38% overall yield through 6 steps involving a hetero Diels-Alder reaction and an aza-Claisen rearrangement.
Preparation method of 4 - amino -2 - cyclopentene -1 - methoxide hydrochloride (by machine translation)
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Paragraph 0019; 0037; 0040-0042; 0045-0047; 0050-0052, (2020/08/18)
The invention provides a preparation method of 4 - amino -2 - cyclopentene -1 - methyl alkoxide, and belongs to the technical field of synthesis of medical intermediates. The preparation method of 4 - amino -2 - cyclopentene -1 - methoxide hydrochloride comprises the following steps: carrying out esterification ring-opening reaction 2 - azabicyclo [2, 2, 1] hep -5 -3 - ketone in the presence of thionyl chloride to obtain the hydrochloride of the ring-opening compound. The ring-opening compound hydrochloride is subjected to a reduction treatment in an aqueous solution of dichloromethane to obtain a reaction liquid containing 4 - amino -2 - cyclopentene -1 - methoxide hydrochloride. The reaction raw material is low in price, and can effectively solve the problem that a large amount of high-cost and high-pollution acid catalysts are required to be used. (by machine translation)
A Mitsunobu reaction to functionalized cyclic and bicyclic N-arylamines
Gill, Daniel M.,Iveson, Matthew,Collins, Ian,Jones, Alan M.
supporting information, p. 238 - 242 (2017/12/26)
The scope of an unexpected Mitsunobu cyclisation to prepare N-arylated Fsp3-enriched azacycles was investigated. In the current study, we have identified whether a pKa-dependent Mitsunobu cyclodehydration or a pKa-independent Mitsunobu intramolecular reaction was in operation. A Mitsunobu reaction, creating a leaving group, followed by intramolecular nucleophilic displacement was determined to be the dominant pathway.
Optical pure amino alcohol hydrochloride preparation method
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Paragraph 0074-0075; 0078, (2017/08/25)
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.
PROCESS FOR THE PREPARATION OF AMINO ALCOHOL DERIVATIVES OR SALTS THEREOF
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Paragraph 0048, (2017/09/02)
The present invention relates to a process for the preparation of amino alcohol derivatives or salts thereof. In particular the present invention relates to process for the preparation of amino alcohol derivatives or salts thereof which may be used as intermediates in the preparation of HIV reverse transcriptase inhibitors, more preferably Carbovir and Abacavir. The present invention more specifically relates to a process for the preparation of (1S,4R)-4-amino-2-cyclopentene-1-methanol of Formula IIIa. The present invention also specifically relates to process for the preparation of Abacavir sulfate of Formula II using compound of Formula IIIa prepared according to the process of the present invention.
An expedient synthesis of oxazepino and oxazocino quinazolines
Hensbergen, Albertus Wijnand,Mills, Vanessa R.,Collins, Ian,Jones, Alan M.
supporting information, p. 6478 - 6483 (2015/11/16)
A synthetic route to a new class of privileged tri- and tetra-cyclic quinazolines containing a medium-sized ring is reported. An expedient synthetic route involving nucleophilic aromatic substitution, and sequential Niementowski and BOP-mediated ring clos
Syntheses of carbocyclic aminonucleosides and (-)-epi-4′-carbocyclic puromycin: application of palladium(0)/indium iodide-allylations and tethered aminohydroxylations
Cesario, Cara,Tardibono Jr., Lawrence P.,Miller, Marvin J.
supporting information; experimental part, p. 3053 - 3056 (2010/08/05)
Carbocyclic aminonucleosides and epi-4′-carbocyclic puromycin were prepared from an acylnitroso-derived hetero Diels-Alder cycloadduct. Pd(0)/InI-mediated allylations of a formyl species were used to install the 4′-hydroxymethyl group. A tethered aminohydroxylation strategy was employed to install the cis-2′,3′-aminoalcohol moiety with complete regio- and diastereocontrol.
Application of phosphoramidate ProTide technology significantly improves antiviral potency of carbocyclic adenosine derivatives
McGuigan, Christopher,Hassan-Abdallah, Alshaimaa,Srinivasan, Sheila,Wang, Yikang,Siddiqui, Adam,Daluge, Susan M.,Gudmundsson, Kristjan S.,Zhou, Huiqiang,McLean, Ed W.,Peckham, Jennifer P.,Burnette, Thimysta C.,Marr, Harry,Hazen, Richard,Condreay, Lynn D.,Johnson, Lance,Balzarini, Jan
, p. 7215 - 7226 (2007/10/03)
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 nucleoside compound
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, (2008/06/13)
The present invention relates to (1R,4S)-4-(6-amino-9H-purin-9-yl)-2-cyclopentene-1-methanol and its use in medical therapy for the treatment of hepatitis B infection.
PHOSPHORAMIDATE, AND MONO-, DI-, AND TRI-PHOSPHATE ESTERS OF (1R, CIS)-4-(6-AMINO-9H-PURIN-9-YL)-2-CYCLOPENTENE-1-METHANOL AS ANTIVIRAL AGENTS
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, (2008/06/13)
The present invention relates to phosphoramidate, and phosphate esters of (1R,cis)-4-(6-amino-9H-purin-9-yl)-2-cyclopentene-1nethanol, processes for their preparation, and their use in treating viral infections.
