127759-89-1

Basic information

• Product Name: Lobucavir
• Synonyms: Lobucavir;(R)-BHCG;2-Amino-9-[(1R)-2α,3β-bis(hydroxymethyl)cyclobutyl]-9H-purin-6(1H)-one;BMS-180194;Carbocyclic oxetanocin G;SQ-34514;6H-Purin-6-one, 2-amino-9-((1R,2R,3S)-2,3-bis(hydroxymethyl)cyclobutyl)-1,9-dihydro-;Ccris 9309
• CAS NO: 127759-89-1
• Molecular Formula: C₁₁H₁₅N₅O₃
• Molecular Weight: 265.272
• Product Categories: Bases & Related Reagents;Heterocycles;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 127759-89-1.mol

Chemical Properties

• Melting Point: 301-306°C
• Boiling Point: 651.8oC at 760 mmHg
• Flash Point: 348oC
• Appearance: /
• Density: 1.92±0.1 g/cm3 (20 oC 760 Torr), Calc.*
• Vapor Pressure: 7.08E-18mmHg at 25°C
• Refractive Index: 1.881
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9?+-.0.20(Predicted)
• CAS DataBase Reference: Lobucavir(CAS DataBase Reference)
• NIST Chemistry Reference: Lobucavir(127759-89-1)
• EPA Substance Registry System: Lobucavir(127759-89-1)

Safety Data

• Hazardous Substances Data: 127759-89-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Lobucavir is used as an antiviral agent for the treatment of viral infections caused by human immunodeficiency virus (HIV), cytomegalovirus (CMV), and herpes virus. Its effectiveness in combating these infections is attributed to its ability to interfere with the viral replication process, thereby limiting the spread of the virus and alleviating the symptoms associated with the infections.

InChI:InChI=1/C11H15N5O3/c12-11-14-9-8(10(19)15-11)13-4-16(9)7-1-5(2-17)6(7)3-18/h4-7,17-18H,1-3H2,(H3,12,14,15,19)/t5-,6-,7-/m1/s1

Upstream product

• 1013657-42-5 C₃₇H₄₆O₅ 
• 1013657-40-3 ((1S,2S,3S)-3-((R)-1-(2,4,6-triisopropylphenyl)ethoxy)-2-((triisopropylsilyloxy)methyl)cyclobutyl)methanol 
• 1013657-41-4 ((1S,2S,3S)-3-(1-(2,4,6-triisopropylphenyl)ethoxy)cyclobutane-1,2-diyl)dimethanol 
• 132294-17-8 <(1S)-(1α,2β,3β)>-3-Hydroxy-1,2-cyclobutanedimethanol 1,2-dibenzoate ester 
• 127696-10-0 trans-3,3-diethoxy-1,2-cyclobutanedicarboxylic acid diethyl ester 
• 132178-71-3 trans-3,3-diethoxy-1,2-cyclobutanedicarboxylic acid 
• 228406-92-6 N,N'-bis[(phenylmethoxy)carbonyl]bis[L-valine], O,O'-[(1S,2R,3R)-3-(2-amino-6-oxo-1H-purin-9-yl)cyclobuta-1,2-diyl]methyl ester 
• 132294-19-0 <1S-(1α,2β,3α)>-3-<2-amino-6-(phenylmethoxy)-9H-purin-9-yl>-1,2-cyclobutanedimethanol 1,2-dibenzoate ester 
• 132332-77-5 6-chloro-9-purine 
• 126261-73-2 C₂₀H₂₀O₅ 
• 126261-74-3 (1α,2β,3β)-3-<<(4-methylphenyl)sulfonyl>oxy>-1,2-cyclobutanedimethanol, dibenzoate ester 
• 64-18-6 formic acid 
• 130368-92-2 (1β,2α,3β)-2,3-bis(tert-butyldimethylsiloxymethyl)cyclobutylamine 
• 1007-99-4 2-amino-6-chloro-5-nitro-3H-pyrimidine-4-one 

Downstream Products

• 228406-92-6 N,N'-bis[(phenylmethoxy)carbonyl]bis[L-valine], O,O'-[(1S,2R,3R)-3-(2-amino-6-oxo-1H-purin-9-yl)cyclobuta-1,2-diyl]methyl ester 

Related news

Regioselective enzymatic aminoacylation of Lobucavir (cas 127759-89-1) to give an intermediate for Lobucavir (cas 127759-89-1) prodrug08/10/2019

Synthesis of lobucavir prodrug, L-valine, [(1S,2R,3R)-3-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-2-(hydroxymethyl)cyclobutyl]methyl ester monohydrochloride (BMS 233866), requires regioselective coupling of one of the two hydroxyl groups of lobucavir (BMS 180194) with valine. Either hydroxyl gro...detailed

Relevant articles and documents

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Azetidinone derivatives for the treatment of HCMV infections

A compound of formula 1: wherein Y is S or O; R1is C1-6alkyl; (C0-6alkyl)aryl; (C0-6alkyl)Het; or R1is an amino acid analog or dipeptide analog of the formula: wherein R2is H, C1-10alkyl; or an amide or ester group; A is C6-10aryl, Het or CH—R3wherein R3is C1-6alkyl or (C0-4alkyl)aryl; and Z is H, C1-6alkyl, or an acyl; R4is hydrogen, lower alkyl, methoxy, ethoxy, or benzyloxy; and R5is alkyl, cycloalkyl, carboxyl group; an aryl; Het or Het(lower alkyl); or R4and R5together with the nitrogen atom to which they are attached form a nitrogen containing ring optionally substituted with phenyl or C(O)OCH2-phenyl, said phenyl ring optionally mono- or di-substituted with among others C(O)OR7wherein R7is lower alkyl or phenyl(lower alkyl); or a therapeutically acceptable acid addition salt thereof which compounds are useful in the treatment of HCMV infections.

Regioselective enzymatic aminoacylation of lobucavir to give an intermediate for lobucavir prodrug

Synthesis of lobucavir prodrug, L-valine, [(1S,2R,3R)-3-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-2-(hydroxymethyl)cyclobutyl]methyl ester monohydrochloride (BMS 233866), requires regioselective coupling of one of the two hydroxyl groups of lobucavir (BMS 180194) with valine. Either hydroxyl group of lobucavir could be selectively aminoacylated with valine by using enzymatic reactions. N-[(Phenylmethoxy)carbonyl]-L-valine, [(1R,2R,4S)-2-(2-amino-6-oxo-1H-purin-9-yl)-4-(hydroxymethyl)cyclobutyl]methyl ester (3, 82.5% yield), was obtained by selective hydrolysis of N,N'-bis[(phenylmethoxy)carbonyl]bis[L-valine], O,O'-[(1S,2R,3R)-3-(2-amino-6-oxo-1H-purin-9-yl)cyclobuta-1,2-diyl]methyl ester (1) with lipase M, and L-valine, [(1R,2R,4S)-2-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-4-(hydroxymethyl)cyclobutyl]methyl ester monohydrochloride (4, 87% yield) was obtained by hydrolysis of bis[L-valine], O,O'-[(1S,2R,3R)-3-(2-amino-6-oxo-1H-purin-9-yl)cyclobuta-1,2-diyl]methyl ester, dihydrochloride (2), with lipase from Candida cylindracea. The final intermediate for lobucavir prodrug, N-[(phenylmethoxy)carbonyl]-L-valine, [(1S,2R,4R)-3-(2-amino-6-oxo-1H-purin-9-yl)-2-(hydroxymethyl)cyclobutyl]methyl ester (5), could be obtained by transesterification of lobucavir using ChiroCLEC(TM) BL (61% yield), or more selectively by using immobilized lipase from Pseudomonas cepacia (84% yield). Copyright (C) 2000 Elsevier Science Ltd.

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