188399-48-6

Basic information

• Product Name: (1s-trans)-2-[(phenylmethoxy)methyl]-3-cyclopenten-1-ol
• Synonyms: (1s-trans)-2-[(phenylmethoxy)methyl]-3-cyclopenten-1-ol;(1R,2S)-2-[(Phenylmethoxy)methyl]-3-cyclopenten-1-ol;(1R-trans)-2-[(Phenylmethoxy)methyl]-3-cyclopenten-1-ol;3-Cyclopenten-1-il, 2-[(phenylmethoxy)methyl]-, (1R-trans);3-Cyclopenten-1-o1，2-[(phenylmethoxy)methyl]-(1R-trans);(1R-trans)3-Cyclopenten-1-ol, 2-[(phenylmethoxy)methyl];Entecavir N-1;(1s-trans)-2-[(pheny
• CAS NO: 188399-48-6
• Molecular Formula: C₁₃H₁₆O₂
• Molecular Weight: 204.26
• Product Categories: Other Products
• Mol File: 188399-48-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 319 ºC
• Flash Point: 135 ºC
• Appearance: /
• Density: 1.112
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.65±0.40(Predicted)
• CAS DataBase Reference: (1s-trans)-2-[(phenylmethoxy)methyl]-3-cyclopenten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1s-trans)-2-[(phenylmethoxy)methyl]-3-cyclopenten-1-ol(188399-48-6)
• EPA Substance Registry System: (1s-trans)-2-[(phenylmethoxy)methyl]-3-cyclopenten-1-ol(188399-48-6)

Safety Data

• Hazardous Substances Data: 188399-48-6(Hazardous Substances Data)

Usage

Description

(1s-trans)-2-[(phenylmethoxy)methyl]-3-cyclopenten-1-ol is a light yellow oil that serves as a crucial reactant in the synthesis of carbocyclic deoxyguanosine analogs. These analogs exhibit potent and selective anti-hepatitis B virus activity, making this compound an important component in the development of antiviral treatments.

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 
• 3587-60-8 Benzyloxymethyl chloride 
• 4984-82-1 sodium cyclopentadienylide 

Downstream Products

• 1061362-37-5 C₂₀H₂₂O₂ 
• 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 
• 1370008-64-2 (1S,2S,4R)-4-(4-((S)-2,3-dihydro-1H-inden-1-ylamino)furo[3,2-d]pyrimidin-7-yl)-2-(sulfamoyloxymethyl)cyclopentyl 4-nitrobenzoate 

Relevant articles and documents

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.

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.