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Usage

Uses

Used in Pharmaceutical Industry:
(1s-trans)-2-[(phenylmethoxy)methyl]-3-cyclopenten-1-ol is used as a reactant for the preparation of carbocyclic deoxyguanosine analogs, which are known for their potent and selective anti-hepatitis B virus properties. This application is significant in the development of effective antiviral therapies to combat hepatitis B virus infections.

InChI:InChI=1/C13H16O2/c14-13-8-4-7-12(13)10-15-9-11-5-2-1-3-6-11/h1-7,12-14H,8-10H2/t12-,13+/m1/s1

Upstream product

• 39939-07-6 5-(benzyloxymethyl)cyclopentadiene 
• 4984-82-1 sodium cyclopentadienylide 
• 3587-60-8 Benzyloxymethyl chloride 

Downstream Products

• 1354695-79-6 [6-Benzyloxy-9-((1R,3S,4R)-4-benzyloxy-3-benzyloxymethyl-2-methylene-cyclopentyl)-9H-purin-2-yl]-[(4-methoxy-phenyl)-diphenyl-methyl]-amine 
• 873298-16-9 (1R,2S,3R,5S)-3-Benzyloxy-2-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane 
• 1370007-75-2 (1R,4S)-2-(benzyloxymethyl)-4-(4-methylsulfanylpyrrolo[2,1-f][1,2,4]triazin-7-yl)cyclopent-2-en-1-ol 
• 1392515-06-8 (1R,4S)-2-(benzyloxymethyl)-4-[4-[[(1S)-indan-1-yl]amino]pyrrolo[2,1-f][1,2,4]triazin-7-yl]cyclopent-2-en-1-ol 
• 1370007-96-7 (1R,2S,4R)-2-(benzyloxymethyl)-4-[4-[[(1S)-indan-1-yl]amino]thieno[3,2-d]pyrimidin-7-yl]cyclopentanol 
• 1370007-98-9 [(1S,2S,4R)-2-(hydroxymethyl)-4-[4-[[(1S)-indan-1-yl]amino]thieno[3,2-d]pyrimidin-7-yl]cyclopentyl]-4-nitrobenzoate 
• 1370008-40-4 (1S,4S)-2-(benzyloxymethyl)-4-(4-((S)-2,3-dihydro-1H-inden-1-ylamino)pyrazolo[1,5-a][1,3,5]triazin-8-yl)cyclopent-2-enol 
• 1370008-55-1 2-((3S,4R)-3-(benzyloxymethyl)-4-(tert-butyldiphenylsilyloxy)-cyclopentyl)acetonitrile 
• 1370008-57-3 3-amino-4-((3S,4R)-3-(benzyloxymethyl)-4-(tert-butyldiphenylsilyloxy)cyclopentyl)furan-2-carbonitrile 
• 1370008-58-4 7-((1R,3S,4R)-3-(benzyloxymethyl)-4-(tert-butyldiphenylsilyloxy)cyclopentyl)-N-((S)-2,3-dihydro-1H-inden-1-yl)furo[3,2-d]pyrimidin-4-amine 
• 1370008-60-8 7-((1S,3S,4R)-3-(benzyloxymethyl)-4-(tert-butyldiphenylsilyloxy)cyclopentyl)-N-((S)-2,3-dihydro-1H-inden-1-yl)furo[3,2-d]pyrimidin-4-amine 
• 1370008-61-9 (1R,2S,4R)-2-(benzyloxymethyl)-4-(4-((S)-2,3-dihydro-1H-inden-1-ylamino)furo[3,2-d]pyrimidin-7-yl)cyclopentanol 
• 1370008-62-0 (1S,2S,4R)-4-(4-((S)-2,3-dihydro-1H-inden-1-ylamino)furo[3,2-d]pyrimidin-7-yl)-2-(hydroxymethyl)cyclopentyl 4-nitrobenzoate 
• 1370008-63-1 (1S,2S,4R)-2-(benzyloxymethyl)-4-(4-((S)-2,3-dihydro-1H-inden-1-ylamino)furo[3,2-d]pyrimidin-7-yl)cyclopentyl 4-nitrobenzoate 

Relevant academic research and scientific papers

N-O bond as a glycosidic-bond surrogate: Synthetic studies toward polyhydroxylated N-alkoxypiperidines

A series of novel polyhydroxylated N-alkoxypiperidines has been synthesized by ring-closing double reductive amination (DRA) of highly functionalized 1,5-dialdehydes with various hydroxylamines. The required saccharide-based dialdehydes were prepared efficiently from sodium cyclopentadienylide in seven steps. A two-step protocol has been developed for the DRA; it led, after deprotection, to isofagomine, 3-deoxyisofagomine, and numerous other N-alkoxy analogues. The barrier to inversion in these polyhydroxylated N-alkoxypiperidine derivatives was found by variable-temperature NMR methods to be approximately 15 kcal mol-1. With the exception of N-hydroxyisofagomine itself, none of the compounds prepared showed significant inhibitory activity against sweet almond β-glucosidase. Copyright

Asymmetric synthesis of polyhydroxylated N -alkoxypiperidines by ring-closing double reductive amination: Facile preparation of isofagomine and analogues

A de novo synthesis of novel polyhydroxylated N-alkoxypiperidines based on the ring-closing double reductive amination of 1,5-dialdehydes, obtained by oxidative cleavage of cyclopentene derivatives, with O-substituted hydroxylamines is reported. Isofagomine was accessed by cleavage of the N-O bond of an N-alkoxypiperidine.

SULFONAMIDE, SULFAMATE, AND SULFAMOTHIOATE DERIVATIVES

The disclosure provides biologically active compounds of formula (I): and pharmaceutically acceptable salts thereof, compositions containing these compounds, and methods of using these compounds in a variety applications, such as treatment of diseases or disorders associated with E1 type activating enzymes, and with Nedd8 activating enzyme (NAE) in particular.

Synthesis of 2′,3′-modified carbocyclic L -nucleoside analogues

New divergent approaches to 2′,3′-modified carbocyclic L-nucleoside analogues starting from enantiomerically pure (1R,2S)- or (1S,2R)-2-(benzyloxymethyl)cyclopent-3-enol are described. In the key step, stereochemically pure cyclopentanols were condensed with N3-protected thymine through a modified Mitsunobu protocol. Moreover, several routes to different cyclopentanol derivatives, to prepare carbocyclic L-2′,3′-didehydro- 2′,3′-dideoxynucleosides (L-d4N), L-2′,3′- dideoxynucleosides (L-ddN), and L-ribonucleosides are reported. Copyright

Cyclopentane-nucleobase coupling in the synthesis of carbocyclic L-nucleosides: Is a SN2-reaction an alternative to the mitsunobu-reaction?

Several carbocyclic L-nucleosides have been synthesized by coupling a cyclopentane-system with heterocycles according to a modified Mitsunobu-protocol. This reaction gave two regioisomers, the N1-alkylated product and an unwanted O2-product. A simple SN2-reaction has been investigated as an alternative for such couplings. Copyright Taylor & Francis Group, LLC.

Removal of pinanol via continuous steam distillation

A practical procedure for the efficient removal of pinanol from the reaction mixture has been developed. The process was based on the observation that pinanol can be easily removed by steam distillation in the laboratory. On-scale, a continuous countercurrent column stripper was implemented to remove pinanol.

BMS-200475, a novel carbocyclic 2'-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro

BMS-200475, a never carbocyclic analog of 2'-deoxyguanosine, is a potent inhibitor of hepatitis B virus in vitro (ED50 = 3 nM) with relatively low cytotoxicity (CC50 = 21-120 μM). A practical 10-step asymmetric synthesis was developed affording BMS-200475 in 18% overall chemical yield and > 99% optical purity. The enantiomer of BMS-200475 as well as the adenine, thymine, and iodouracil analogs are much less active.