146609-12-3

Basic information

• Product Name: 4-amino-1-[(2S,4R)-4-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one
• CAS NO: 146609-12-3
• Molecular Formula: C₉H₁₃N₃O₃
• Molecular Weight: 211.2178
• Mol File: 146609-12-3.mol

Chemical Properties

• Boiling Point: 415°C at 760 mmHg
• Flash Point: 204.8°C
• Density: 1.57g/cm³
• Vapor Pressure: 1.27E-08mmHg at 25°C
• Refractive Index: 1.686
• CAS DataBase Reference: 4-amino-1-[(2S,4R)-4-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-1-[(2S,4R)-4-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one(146609-12-3)
• EPA Substance Registry System: 4-amino-1-[(2S,4R)-4-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one(146609-12-3)

Safety Data

• Hazardous Substances Data: 146609-12-3(Hazardous Substances Data)

Upstream product

• 55387-85-4 3-hydroxymethyl-4-hydroxybutanal diethyl acetal 
• 155165-12-1 5(S)-<2,4(1H,3H)-pyrimidinedione>tetrahydro-3(S)-<(((1,1-dimethylethyl)dimethylsilyl)oxy)methyl>furan 
• 134665-17-1 (S)-2-(acetoxymethyl)-4,4-diethoxybutyl pivalate 
• 134665-25-1 1-O-acetyl-5-O-pivaloyl-(3S)-2,3-dideoxyapiose 
• 134665-18-2 (2-hydroxy-4-(S)-tetrahydrofuranyl)methyl pivalate 
• 144461-19-8 (R)-2-(2,2-diethoxyethyl)-1,3-propanediol monoacetate 
• 155101-91-0 2,2-Dimethyl-propionic acid (3S,5S)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl ester 
• 155165-09-6 4-Amino-1-[(2S,4S)-4-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidin-2-one 
• 133838-13-8 Benzoic acid (3R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl ester 
• 485815-81-4 Benzoic acid 5-methoxy-tetrahydro-furan-3-ylmethyl ester 
• 143724-42-9 (rel)-(1S/1R,3S)-(tetrahydro-1-methoxyfuran-3-yl)methanol 
• 99776-32-6 2-(hydroxymethyl)-4,4-dimethoxybutan-1-ol 
• 133725-52-7 Benzoic acid (3R,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl ester 
• 133725-52-7 Benzoic acid (3S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl ester 

Relevant articles and documents

Synthetic approaches to novel cis and trans dideoxynucleosides of the apiose family

Stereoselective synthesis of the complete family of optically active dideoxygenated nucleosides of the apiose family have been developed. The chiral aldodiol system 7, a key intermediate in this synthesis, was prepared from the prochiral molecule 6, through the action of the lipase from Candida cylindracia. Approaches to novel enantiomeric and diastereoisomeric dideoxynucleosides containing the tetrahydrofuranethanol moiety have also been discovered. A key intermediate in this approach was the optically active trans-allyllactone 61, prepared from L-glutamic acid, and its isomerization product, the corresponding cis-allylbutyrolactone 62. The methodologies developed have generality and allow synthetic access to a wide variety of new nucleosides.

Synthesis of optically active nucleoside analogs containing 2,3- dideoxyapiose in the presence of a catalytic amount of trimethylsilyl iodide

Optically pure (R)-4,4-diethoxy-2-(hydroxymethyl)butyl acetate (1) was synthesized enantioselectively by lipase-catalyzed transesterification from 4,4-diethoxy-2-(hydroxymethyl)butanol. Coupling of silylated nucleobases and 2-O-acetyl-5-O-pivaloyl-(3S)-2,

Novel isomeric dideoxynucleosides of the D- and L-apiose family

Short synthetic approaches to optically active, cis and trans dideoxynucleoside analogs of the D- and L-apiose family have been developed. The chiral precursor for the syntheses was the enzymatically prepared compound, S(-)-2-(2-propenyl)-1,3-propanediol monoacetate (5).

SYNTHESIS OF (+/-)-2'-OXA-CARBOCYCLIC-2',3'-DIDEOXYNUCLEOSIDES AS POTENTIAL ANTI-HIV AGENTS

Novel 2',3'-dideoxynucleosides, having the pentofuranosyl oxygen at the 2'-position, were obtained by a short synthetic route from diethyl malonate and bromoacetalehyde dimethyl acetal.The results of biological testing against HIV-1 in vitro are presented.