213769-47-2

Upstream product

• 4836-13-9 N₄-benzoyl-2'-deoxycytidine 
• 100-52-7 benzaldehyde 
• 951-77-9 2'-Deoxycytidine 
• 64911-18-8 3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine 
• 3992-42-5 2'-deoxycytidine monohydrochloride 
• 100-46-9 benzylamine 

Downstream Products

• 958-09-8 2'-deoxy-D-adenosine 
• 3413-66-9 α-deoxyadenosine 
• 92574-65-7 3',5'-di-O-acetyl-N₄-benzoyl-α-2'-deoxycytidine 
• 23526-11-6 S-methylthiodeoxyinosine 
• 51549-47-4 3',5'-di-O-acetyl-N₄-benzoyl-2'-deoxycytidine 

Relevant academic research and scientific papers

Facile functionalization at the C4 position of pyrimidine nucleosides via amide group activation with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and biological evaluations of the products

Reactions of O-t-butyldimethylsilyl-protected thymidine, 2′-deoxyuridine, and 3′-azidothymidine (AZT) with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) leads to activation of the C4 amide carbonyl by formation of putative O4-(benzotriazol-1-yl) derivatives. Subsequent substitution with alkyl and aryl amines, thiols, and alcohols leads to facile functionalization at this position. Reactions with amines and thiols were conducted either as a two-step, one-pot transformation, or as a one-step conversion. Reactions with alcohols were conducted as two-step, one-pot transformations. In the course of these investigations, the formation of 1-(4-pyrimidinyl)-1H-benzotriazole-3-oxide derivatives from the pyrimidine nucleosides was identified. However, these too underwent conversion to the desired products. Products obtained from AZT were converted to the 3′-amino derivatives by catalytic reduction. All products were assayed for their abilities to inhibit cancer cell proliferation and for antiviral activities. Many were seen to be active against HIV-1 and HIV-2, and one was active against herpes simplex virus-1 (HSV-1).

Convenient and efficient syntheses of N6-and N 4-substituted adenines and cytosines and their 2-deoxyribosides

Convenient and efficient methods of the synthesis of N6-and N4-substituted derivatives of adenine and cytosine and their 2-deoxyribosides were developed. The reactions of either unprotected nucleobases (adenine, cytosine) or unprotected 2-deoxyribosides with aryl or alkyl aldehydes give corresponding Schiff bases that can be reduced to the target title compounds with high overall yields. In the case of aryl aldehydes the imine derivatives are obtained in the presence of methoxides in methanol and reduced with sodium borohydride. The corresponding reactions with alkyl aldehydes require the use of acetic acid and borane dimethyl sulfide complex instead.

Rapid and selective reduction of amide group by borane-amine complexes in acyl protected nucleosides

Borane-amine complexes provide an unusually fast and selective reduction of a deoxynucleoside N-acyl group to a corresponding N-alkyl group. Three different nucleosides (dG, dA, and dC) each having one of three N-protecting groups (benzoyl, isobutyryl, or acetyl) were used to prepare N-alkylated nucleosides in good yields under mild conditions. Deoxyribose O-acyl protecting groups remain intact at the conditions of N-acyl group reduction.

Modified nucleic acid amplification primers

The present invention provides modified primers for use in the amplification of a nucleic acid sequence. Amplifications carried out using the modified primers result in less non-specific amplification product, in particular, primer dimer, and a concomitan