77244-83-8

Basic information

• Product Name: Adenosine, N-benzoyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-
• CAS NO: 77244-83-8
• Molecular Formula: C33H35N5O5Si
• Molecular Weight: 609.757
• Mol File: 77244-83-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Adenosine, N-benzoyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Adenosine, N-benzoyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-(77244-83-8)
• EPA Substance Registry System: Adenosine, N-benzoyl-5'-O-[(1,1-dimethylethyl)diphenylsilyl]-(77244-83-8)

Safety Data

• Hazardous Substances Data: 77244-83-8(Hazardous Substances Data)

Upstream product

• 118684-36-9 O^2;_,O3'_,O5'-tris-trimethylsilyl-N⁶-benzoyladenosine 
• 98-88-4 benzoyl chloride 
• 10457-15-5 O^2'_,O3'_,O5'-tris-trimethylsilanyl-adenosine 
• 58-61-7 adenosine 
• 4546-55-8 N-[9-((2R,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 4546-55-8 N-benzoyladenosine 

Downstream Products

• 160905-79-3 6-N-benzoyl-5'-O-(tert-butyldiphenylsilyl)-2',3'-bis-O-(9-phenylxanthen-9-yl)adenosine 
• 80615-02-7 Acetic acid (2R,3S,4S,5R)-2-(6-benzoylamino-purin-9-yl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-iodo-tetrahydro-furan-3-yl ester 
• 214039-18-6 Benzoic acid 2-[(3aR,4R,6R,6aR)-4-(6-benzoylamino-purin-9-yl)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-tetrahydro-furo[3,4-d][1,3]dioxol-2-yl]-ethyl ester 
• 214039-17-5 Benzoic acid (3aR,4R,6R,6aR)-4-(6-benzoylamino-purin-9-yl)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-tetrahydro-furo[3,4-d][1,3]dioxol-2-ylmethyl ester 
• 69293-36-3 N⁶-benzoyl-9-(2',3'-di-O-acetyl-β-D-ribofuranosyl)adenine 
• 76902-49-3 N-(9-((2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide 
• 77244-85-0 2'-O-acetyl-N⁶-benzoyl-3'-deoxyadenosine 
• 80615-03-8 Acetic acid (2R,3R,5S)-2-(6-benzoylamino-purin-9-yl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester 
• 1415645-67-8 (2′R,6′S)-N⁶-benzoyl-9-{6′-[(tert-butyldiphenylsilyloxy)methyl]-N-tritylmorpholin-2′-yl}adenine 
• 956139-16-5 (2′R,6′S)-N⁶-benzoyl-9-[6′-(hydroxymethyl)-N-tritylmorpholin-2′-yl]adenine 
• 1332728-57-0 6-N-benzoyl-9-(2-O-benzoyloxymethoxymethyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)adenine 
• 1332728-59-2 6-N-benzoyl-9-(3-O-benzoyloxymethoxymethyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)adenine 

Relevant articles and documents

Targeting Mycobacterium tuberculosis Biotin Protein Ligase (MtBPL) with Nucleoside-Based Bisubstrate Adenylation Inhibitors

Mycobacterium tuberculosis (Mtb), responsible for both latent and symptomatic tuberculosis (TB), remains the second leading cause of mortality among infectious diseases worldwide. Mycobacterial biotin protein ligase (MtBPL) is an essential enzyme in Mtb and regulates lipid metabolism through the post-translational biotinylation of acyl coenzyme A carboxylases. We report the synthesis and evaluation of a systematic series of potent nucleoside-based inhibitors of MtBPL that contain modifications to the ribofuranosyl ring of the nucleoside. All compounds were characterized by isothermal titration calorimetry (ITC) and shown to bind potently with KDs ≤ 2 nM. Additionally, we obtained high-resolution cocrystal structures for a majority of the compounds. Despite fairly uniform biochemical potency, the whole-cell Mtb activity varied greatly with minimum inhibitory concentrations (MIC) ranging from 0.78 to >100 μM. Cellular accumulation studies showed a nearly 10-fold enhancement in accumulation of a C-2′-α analogue over the corresponding C-2′-β analogue, consistent with their differential whole-cell activity.

Efficient synthesis of protected 3′-deoxyadenosine and 3′-deoxyguanosine from adenosine and guanosine

Highly efficient synthesis of protected 3′-deoxyadenosine and 3′-deoxyguanosine from adenosine and guanosine were described. The 2′,3′-diol of protected adenosine and guanosine were reacted with α-acetoxyisobutyryl bromide to yield 9-(2′-O-acetyl-3′-bromo

Novel Solid-phase Synthesis of Branched Oligoribonucleotides, including a Substrate for the RNA Debranching Enzyme

An effective new route for synthesizing branched oligoribionucleotides in the solid phase in the 5' to 3' direction has been developed.This required the synthesis of reversed monomers, viz. protected nucleoside 5'-phosphoramidites bearing 2'-O-Fpmp and 3'