129732-90-7

Usage

Chemical Properties

Off-White Solid

Uses

Protected Deoxyguanosine.

Upstream product

• 100-39-0 benzyl bromide 
• 961-07-9 2'-Deoxyguanosine 
• 4318-05-2 2-(acetylamino)-9-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one 
• 69992-10-5 3',5'-di-O-acetyl-2'-deoxyguanosine 
• 193092-29-4 Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(2-acetylamino-6-benzyloxy-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 160363-14-4 N-[6-Benzyloxy-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-acetamide 
• 144640-75-5 3',5'-di-O-acetyl-O⁶-benzyl-2'-deoxyguanosine 

Downstream Products

• 1008127-65-8 N²-[1-(3,4-dibenzyloxybenz[a]anthracenyl)]-2'-deoxy-(6-benzyloxy)-guanosine 
• 144640-76-6 O⁶-benzyl-2-fluoro-2'-deoxyinosine 

Relevant academic research and scientific papers

Effect of ionic state of 2'-deoxyguanosine and solvent on its aralkylation by benzyl bromide

To extend studies of the aralkylation of nucleic acid components under a variety of solvent conditions, we determined product distributions from the reactions of benzyl bromide with 2'-deoxyguanosine and the anion of 2'- deoxyguanosine in 2,2,2-trifluoroethanol (TFE) and compared these distributions with those from the reaction of the anion with benzyl bromide in N,N-dimethylacetamide (DMA). 7-Benzylguanine was the only benzylated product detected in the reaction with the neutral nucleoside in TFE. In striking contrast, the reaction of the anion of 2'-deoxyguanosine with benzyl bromide in TFE produced N2-benzyl-2'-deoxyguanosine in significant yield and with high selectivity. The reaction of the anion of 2'-deoxyguanosine with benzyl bromide in DMA produced products derived only from reaction at the 1- and/or 7-position of the nucleoside. The weakly nucleophilic but protic polar solvent TFE and the iminolate tautomeric form of the 2'-deoxyguanosine anion appear to be essential for benzylation at the exocyclic N2-position.

BETA-GLUGURONIDASE CLEAVABLE PRODRUGS OF O6-ALKYLGUANINE-DNA ALKYLTRANSFERASE INACTIVATORS

Disclosed are prodrugs of inactivators of 06-alkylguanine-DNA alkyltransferase (AGT). The prodrugs are cleavable by the (3-glucuronidase enzyme, which is either administered to the patient or produced by necrotic tumor cells. The prodrugs are r

O6-(Alkyl/aralkyl)guanosine and 2'-deoxyguanosine derivatives: Synthesis and ability to enhance chloroethylnitrosourea antitumor action

A series of O6-(alkyl/aralkyl)guanosines and 2'-deoxyguanosine analogs extended to peracetyl and N2-acetyl derivatives, potentially water soluble, was synthesized. Each was associated with N'-(2-chloroethyl)-N-[2- (methylsulfonyl)eth

Epoxide and diol epoxide adducts of polycyclic aromatic hydrocarbons at the exocyclic amino group of deoxyguanosine

Synthesis and separation of the diastereomeric trans N2-2'-deoxyguanosine adducts of tetrahydrophenanthrene 3,4-epoxide and benzo[a]pyrene 7,8-diol 9,10-epoxide (benzylic hydroxyl group and epoxide oxygen trans), as well as the incorporation of