56888-92-7

Upstream product

• 847911-24-4 guanosyl-(3',3')-(2'-amino-2'-deoxyuridine) 
• 26929-65-7 2'-azido-2'-deoxyuridine 

Downstream Products

• 60966-26-9 2'-amino-2'-deoxyguanosine 
• 76727-51-0 9-(2-amino-2-deoxy-β-D-ribofuranosyl)-2-chlorohypoxanthine 
• 171502-14-0 2'-deoxy-2'-(3-methoxybenzamido)uridine 
• 1261083-58-2 2'-deoxy-2'-[3-(2-furyl)-2-azapropanamido]-5'-O-(4,4-dimethoxytrityl)uridin-3'-yl-(2-cyanoethyl N,N-diisopropylphosphoramidite) 
• 1312415-82-9 C₃₆H₃₆N₄O₉ 
• 282543-37-7 2,2-dimethyl-propionic acid 3-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-ylcarbamoyl]-2-oxo-2H-chromen-7-yl ester 
• 282543-36-6 7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid [5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-yl]-amide 
• 333998-14-4 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid [(2R,3R,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-yl]-amide 
• 501353-62-4 2'-N-(N-allyloxycarbonylphenylalanyl)-2'-amino-2'-deoxy-5'-dimethoxytrityluridine 
• 807370-40-7 2'-[N,N-bis(2-methoxyoxalylaminoethyl)aminoethyl]-5'-O-(4,4'-dimethoxytrityl)aminooxalylamino-2'-deoxyuridine 
• 177980-14-2 5'-O-(4,4'-dimethoxytrityl)-2'-methoxyoxalylamido-3'-(2-cyanoethyl-N,N-diisopropylamino)phosphinyl-2'-deoxyuridine 
• 177980-12-0 5'-O-(4,4'-dimethoxytrityl)-2'-methoxyoxalylamido-2'-deoxyuridine 
• 118849-17-5 5'-O-(4,4'-dimethoxytrityl)-2'-(trifluoroacetylamido)-2'-deoxyuridine 
• 174221-86-4 5'-O-dimethoxytrityl-2'-amino-2'-deoxyuridine 

Relevant academic research and scientific papers

Efficient reduction of azides to amines with tributylstannane. High-yield syntheses of amino and diamino deoxynucleosides

Treatment of unprotected azido-deoxynucleosides with tributylstannane/AIBN in hot benzene/DMAC (or silyl-protected derivatives in benzene) resulted in formation of the corresponding amino-deoxynucleosides in high isolated yields. A radical process is indicated.

Phosphodiester cleavage of guanylyl-(3′,3′)-(2′-amino- 2′-deoxyuridine): Rate acceleration by the 2′-amino function

Hydrolytic reactions of the structural analogue of guanylyl-(3′, 3′)-uridine, guanylyl-(3′,3′)-(2′-amino-2′- deoxyuridine), having one of the 2′-hydroxyl groups replaced with an amino function, have been followed by RP HPLC in the pH range 0-13 at 90°C. The results are compared to those obtained earlier with guanylyl-(3′,3′) -uridine, guanylyl-(3′,3′)-(2′,5′-di-O-methyluridine), and uridylyl-(3′,5′)-uridine. Under basic conditions (pH > 8), the hydroxide ion-catalyzed cleavage of the P-O3′ bond (first-order in [OH-]) yields a mixture of 2′-amino-2′-deoxyuridine and guanosine 2′,3′-cyclic phosphate which is hydrolyzed to guanosine 2′- and 3′-phosphates. Under these conditions, guanylyl-(3′, 3′)-(2′-amino-2′-deoxyuridine) is 10 times less reactive than guanylyl-(3′,3′)-uridine. Under acidic and neutral conditions (pH 3-8), where the pH-rate profile for the cleavage consists of two pH-independent regions (from pH 3 to pH 4 and from 6 to 8), guanylyl-(3′,3′)- (2′-amino-2′-deoxyuridine) is considerably reactive. For example, in the latter pH range, guanylyl-(3′,3′)-(2′-amino-2′- deoxyuridine) is more than 2 orders of magnitude more labile than guanylyl(3′,3′)-(2′,5′-di-O-methyluridine), while in the former pH range the reactivity difference is 1 order of magnitude. Under very acidic conditions (pH +]) compete with the cleavage. The Zn2+-promoted cleavage ([Zn2+] = 5 mmol L-1) is 15 times faster than the uncatalyzed reaction at pH 5.6. The mechanisms of the reactions of guanylyl-(3′,3′)-(2′-amino-2′-deoxyuridine) are discussed, particularly focusing on the possible stabilization of phosphorane intermediate and/or transition state via an intramolecular hydrogen bonding by the 2′-amino group.