18055-47-5

Usage

Uses

Used in Pharmaceutical Research and Development:
Benzamide, N-(trimethylsilyl)-N-[9-(trimethylsilyl)-9H-purin-6-yl]is used as an intermediate in the synthesis of 2,3,5-Tri-O-acetyl α-Adenosine (T733805) for the development of Adenosine (A280400(P)) impurities. This application is crucial for advancing pharmaceutical research and improving the purity and effectiveness of adenosine-related compounds in various therapeutic applications.

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 4005-49-6 N-benzoyladenine 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 66224-66-6 adenine 
• 93-97-0 benzoic acid anhydride 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 109923-78-6 6-N-benzoyl-2',3',5'-tri-O-benzoyl-β-L-adenosine 
• 128119-35-7 C₃₇H₂₇N₅O₇ 
• 128163-32-6 C₃₇H₂₇N₅O₇ 
• 124288-89-7 (2S,5S)-5-Azido-6-[(2R,3R,4R,5R)-3,4-diacetoxy-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-2-yl]-2-(toluene-4-sulfonylamino)-hexanoic acid tert-butyl ester 
• 69293-36-3 N⁶-benzoyl-9-(2',3'-di-O-acetyl-β-D-ribofuranosyl)adenine 
• 132820-74-7 Acetic acid (3R,4R,5R)-4-acetoxy-2-(6-benzoylamino-purin-9-yl)-5-[1-(2,2,2-trifluoro-acetyl)-pyrrolidin-3-ylmethyl]-tetrahydro-furan-3-yl ester 
• 132820-78-1 Acetic acid (3R,4R,5R)-4-acetoxy-2-(6-benzoylamino-purin-9-yl)-5-[2,4-bis-(2,2,2-trifluoro-acetylamino)-butyl]-tetrahydro-furan-3-yl ester 
• 132820-76-9 Acetic acid (3R,4R,5R)-4-acetoxy-2-(6-benzoylamino-purin-9-yl)-5-{4-(2,2,2-trifluoro-acetylamino)-2-[(2,2,2-trifluoro-acetylamino)-methyl]-butyl}-tetrahydro-furan-3-yl ester 
• 112668-60-7 N6-benzoyl-9-(2'-O-benzoyl-3'-deoxy-3'-fluoro-β-D-ribofuranosyl)adenine 
• 6984-53-8 N⁶,2',3',5'-tetra-O-benzoyladenosine 
• 134665-21-7 2,2-Dimethyl-propionic acid (S)-5-(6-benzoylamino-purin-9-yl)-tetrahydro-furan-3-ylmethyl ester 
• 138348-89-7 9-(1-O-acetyl-3,4-O-isopropylidene-6-O-pivaloyl-α-D-psicofuranosyl)-N⁶-benzoyladenine 
• 138348-88-6 9-(1-O-acetyl-3,4-O-isopropylidene-6-O-pivaloyl-β-D-psicofuranosyl)-N⁶-benzoyladenine 
• 138348-92-2 9-(1,3,4-tri-O-acetyl-6-O-pivaloyl-α-D-psicofuranosyl)-N⁶-benzoyladenine 

Relevant academic research and scientific papers

Efficient Synthesis of α-Purine Nucleosides of 2-Deoxyribofuranose and 2-Deoxyribopyranose

A high yield synthesis of α-purine nucleosides of 2-deoxyribofuranose and 2-deoxyribopyranose is reported starting from 1,3,5-tri-O-acetyl-2-deoxyribofuranose and 1,3,5-tri-O-acetyl-2-deoxyribopyranose with silylated purines under Lewis acid (SnCl4) catal

Amino-thiocyanation of electron rich olefins as an efficient purine and pyrimidine N-alkylation process

This work describes a relatively simple process to form thiocyanate substituted nucleoside mimics. CISCN is slowly added to a solution of silylated heterocycle and suitable electron rich alkene. N-alkylated heterocycles are isolated in good yields after hydrolytic workup and flash chromatography.

Analogues of the natural product sinefungin as inhibitors of EHMT1 and EHMT2

A series of analogues of the natural product sinefungin lacking the amino acid moiety was synthesized and probed for their ability to inhibit EHMT1 and EHMT2. This study led to inhibitors 3b and 4d of methyltransferase activity of EHMT1 and EHMT2 and it demonstrates that such analogues constitute an interesting scaffold to develop selective methyltransferase inhibitors. Surprisingly, the inhibition was not competitive toward AdoMet.

2′-deoxy-2′-α-C-(hydroxymethyl)adenosine as potential anti-HCV agent

Because of the importance of C-branched nucleosides in the discovery of new antiviral molecules, we decided to synthesize 2′-deoxy-2′-α- C-(hydroxymethyl)adenosine as a potential anti-HCV agent. The synthesis of a new adenosine analogue following two different synthetic routes is described. The new C-branched nucleoside was tested for its antiviral activity and found to be inactive.

Synthesis and antiviral evaluation of α-l-2′- deoxythreofuranosyl nucleosides

The synthesis of a series of α-l-2′-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-α-l-threose, involving a Vorbru?ggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and Mycobacterium tuberculosis thymidylate kinase.

Synthesis of spiroacetal-nucleosides as privileged natural product-like scaffolds

The elaboration of a 6,6-spiroacetal scaffold to incorporate a nucleoside unit at the anomeric position is described. The novel spiroacetal-nucleoside hybrids 11 were generated via nucleosidation of acetoxy-spiroacetal 10 with a series of silylated nucleobases under Vorbrueggen conditions.

Synthesis of optically active 1,4-dioxane nucleotide analogs

Optically active nucleotide analogs were prepared that were composed of a 1,4-dioxane ring as the sugar analog to which either uracil or adenine attached together with two carboxylic ester groups, to be used as vehicles for formation of oligomers. The chiral 1,4-dioxane moiety was constructed from dimethyl L-tartrate via the corresponding (2R,3R)-dimethyl 2-O-allyl-tartrate. Copyright Taylor & Francis Group, LLC.

Synthesis and conformational analysis of 1′- and 3′-substituted 2-deoxy-2-fluoro-D-ribofuranosyl nucleosides

Convergent syntheses of the 9-(3-X-2,3-dideoxy-2-fluoro-β-D- ribofuranosyl)adenines 5 (X = N3) and 7 (X = NH2), as well as of their respective α-anomers 6 and 8, are described, using methyl 2-azido-5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-ribofuranoside (4) as glycosylating agent. Methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-β-D- ribofuranoside (12) was prepared starting from two precursors, and coupled with silylated N6-benzoyladenine to afford, after deprotection, 2′,3′-dideoxy-2′,3′-difluoroadenosine (13). Condensation of 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranose (14) with silylated N2-palmitoylguanine gave, after chromatographic separation and deacylation, the N7-β-anomer 17 as the main product, along with 2′-deoxy-2′-fluoroguanosine (15) and its N9-α- anomer 16 in a ratio of ca. 42:24:10. An in-depth conformational analysis of a number of 2,3-dideoxy-2-fluoro-3-X-D-ribofuranosides (X = F, N3, NH2, H) as well as of purine and pyrimidine 2-deoxy-2-fluoro-D- ribofuranosyl nucleosides was performed using the PSEUROT (version 6.3) software in combination with NMR studies.

Synthesis of 2′-deoxy-2′-C-α-methylpurine nucleosides

2′-Deoxy-2′-C-α-methylribonucleosides provide valuable biochemical probes with which to study RNA structure and function. Using methyl 2-acetoxymethyl-3,5-di-O-(tert-butyldimethylsilyl)-D-ribofuranoside (1) as a glycosylating agent, we achieved in four st

Nucleotides. LXXIV* synthesis of α-D-arabino-oligonucleotides

□ The 5 α-D-arabinofuranosylnucleosides α-araU (15), α-araT (18), α-araC (22), α-araA (25), and α-araG (28) have been synthesized by the modified silyl-method. The amino groups at the nucleobases and the 2′-hydroxy group at the sugar moiety were protected by the 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) group (37-40) and the amide function in α-araG was additionally blocked by the 2-(4-nitrophenyl)ethyl group (63) to improve solubility in organic solvents. Mono-and dimethoxytritylation of the 5′-OH group was performed in the usual manner to give 41-48, 64, and 65 in high yields and further substitution of the 3′-OH group led to the monomeric building blocks 66-75 as well as the 3′-O-succinoyl derivatives 76-85 functioning as starting units in solid-support oligonucleotide synthesis. A large number of oligo-α- arabinonucleotides have been prepared on modified CPG-material applying the npeoc/npe strategy as a very efficient synthetic tool for highly purified, homogenous oligomers. Hybridizations between α-arabinonucleotide strands revealed in analogy to earlier findings an antiparallel orientation whereas the combination of an oligo-α-D-arabinonucleotide with a complementary oligo-2′-deoxy-β-D-ribofuranosylnucleotide showed base-pairing only if a parallel polarity was present. The advantages in oligo-α-arabino- nucleotide synthesis were furthermore demonstrated by the synthesis of the tα-ANAhis a structural analog of the natural tRNAhis of the phage T5. Copyright Taylor & Francis Group, LLC.