110567-23-2

Basic information

• Product Name: (1S,2S,3S,5S)-5-Azido-3-(phenylMethoxy)-2-[(phenylMethoxy)Methyl]cyclopentanol
• Synonyms: (1S,2S,3S,5S)-5-Azido-3-(phenylMethoxy)-2-[(phenylMethoxy)Methyl]cyclopentanol;[1S-(1α,2β,3α,5β)]-5-Αzido-3-(phenylMethoxy)-2-[(phenylMethoxy)Methyl]-cyclopentanol
• CAS NO: 110567-23-2
• Molecular Formula: C₂₀H₂₃N₃O₃
• Molecular Weight: 353
• Product Categories: Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Nucleotides, Bases & Related Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 110567-23-2.mol

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane
• CAS DataBase Reference: (1S,2S,3S,5S)-5-Azido-3-(phenylMethoxy)-2-[(phenylMethoxy)Methyl]cyclopentanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,3S,5S)-5-Azido-3-(phenylMethoxy)-2-[(phenylMethoxy)Methyl]cyclopentanol(110567-23-2)
• EPA Substance Registry System: (1S,2S,3S,5S)-5-Azido-3-(phenylMethoxy)-2-[(phenylMethoxy)Methyl]cyclopentanol(110567-23-2)

Safety Data

• Hazardous Substances Data: 110567-23-2(Hazardous Substances Data)

Usage

Chemical Properties

Colorless Oil

Upstream product

• 110567-22-1 (2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane 

Downstream Products

• 110567-27-6 <1R-(1α,2β,3α,4β)>-5-fluoro-3-(phenylmethoxy)-2-<(phenylmethoxy)methyl>-1-cyclopentanamine 
• 110567-26-5 <1S-(1α,2β,3α,4β)>-2-fluoro-4-(phenylmethoxy)-3-<(phenylmethoxy)methyl>-1-cyclopentanamine 
• 179761-46-7 Benzoic acid (1S,2R,3S,5S)-5-azido-3-benzyloxy-2-benzyloxymethyl-cyclopentyl ester 
• 888015-86-9 (1S,2S,3S,5S)-5-amino-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol 
• 123169-17-5 1-((1S,2S,3R,4S)-4-Benzyloxy-3-benzyloxymethyl-2-fluoro-cyclopentyl)-1H-pyrimidine-2,4-dione 
• 110612-90-3 (1S,2R,3R,4S)-1-azido-4-benzyloxy-3-benzyloxymethyl-2-fluorocyclopentane 
• 179761-48-9 Benzoic acid (1S,2R,3S,5S)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyl ester 
• 187660-90-8 Benzoic acid (1S,2R,3S,5S)-3-benzyloxy-2-benzyloxymethyl-5-[3-((Z)-3-methoxy-2-methyl-acryloyl)-ureido]-cyclopentyl ester 
• 179761-45-6 Benzoic acid (1S,2R,3S,5S)-3-benzyloxy-2-benzyloxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopentyl ester 
• 169235-65-8 Benzoic acid (1S,2R,3S,5S)-5-amino-3-benzyloxy-2-benzyloxymethyl-cyclopentyl ester 
• 888015-90-5 2-amino-4-methoxy-6-[(1α,2β,3α,4β)-2-hydroxy-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopentyl]amino-5-aminopyrimidine 
• 888015-87-0 (1S,2S,3S,5S)-5-(2-amino-6-chloropyrimidin-4-yl)amino-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol 

Relevant articles and documents

Synthesis of [13C4]Baraclude (entecavir)

Entecavir, labeled as 1H-[13C4]purin-6(9H)-one, was prepared from commercially available [13C]guanidine HCl, 1 and diethyl [1,2,3-13C3]malonate, 2. The reagents were condensed together to give 2-amino-4,6-dichloro[2,4,5,6-13C 4]pyrimidine 3, which in turn was coupled to an optically active amino cyclopentanol derivative, 9. A further sequence of eight reaction steps completed the constructions of the purine ring system and the exocyclic olefin attachment on the cyclic pentyl portion, 18. The removal of the methoxide and benzyl protecting groups gave [13C4]entecavir, 20 in an overall yield of 6.8%. The chemical purity of the title compound was determined by HPLC to be 99.23%. The percent isotopic [13C4] abundance was found by mass spectral analysis to be 96.7%. No detectable level of the unlabeled entecavir was found by LC-MS analysis. Copyright

Synthesis of [14C]-radiolabelled entecavir

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Use of Diethylaminosulphur Trifluoride (DAST) in the Preparation of Synthons of Carbocyclic Nucleosides

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