125084-70-0

Basic information

• Product Name: 9-<2,3-anhydro-5-O-<(tert-butyl)diphenylsilyl>-β-D-ribofuranosyl>adenine
• Synonyms: 9-<2,3-anhydro-5-O-<(tert-butyl)diphenylsilyl>-β-D-ribofuranosyl>adenine
• CAS NO: 125084-70-0
• Molecular Weight: 487.633
• Mol File: 125084-70-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 9-<2,3-anhydro-5-O-<(tert-butyl)diphenylsilyl>-β-D-ribofuranosyl>adenine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-<2,3-anhydro-5-O-<(tert-butyl)diphenylsilyl>-β-D-ribofuranosyl>adenine(125084-70-0)
• EPA Substance Registry System: 9-<2,3-anhydro-5-O-<(tert-butyl)diphenylsilyl>-β-D-ribofuranosyl>adenine(125084-70-0)

Safety Data

• Hazardous Substances Data: 125084-70-0(Hazardous Substances Data)

Upstream product

• 58-61-7 adenosine 
• 2627-64-7 9-(2,3-anhydro-β-D-ribofuranosyl)adenine 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 557771-59-2 (2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3-yl acetate 

Downstream Products

• 71508-05-9 3'-L-(p-methoxyphenylalanylamino)-3'-deoxy-β-D-adenosine 
• 1273196-89-6 5'-O-(tert-butyldiphenylsilyl)-3'-[N-(9-fluorenyl)methoxycarbonyl-O-methyl-L-tyrosyl]amido-3'-deoxyadenosine 
• 1273196-87-4 3'-amino-5'-O-(tert-butyldiphenylsilyl)-3-deoxyadenosine 
• 1273196-85-2 C₂₉H₃₂N₆O₄Si 
• 1273196-83-0 9-[3-bromo-5-O-tert-butyldiphenylsilyl-3-deoxy-2-O-(N-vinylcarbamoyl)-β-D-xylofuranosyl]adenine 
• 68950-21-0 9-(3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-β-D-xylofuranos-1-yl)adenine 
• 141684-87-9 9-[5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl]adenine 
• 226917-54-0 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 226917-53-9 3'-deoxy-3'-(hexadecanoylamino)-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 
• 226917-55-1 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 

Relevant articles and documents

High-yield synthesis of 3'-amino-3'-deoxynucleosides. Conversion of adenosine to 3'-amino-3'-deoxyadenosine

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Synthesis of a xylo-puromycin analogue

N6-Bis-demethylated xylo-puromycin analogue 2 was synthesized over six steps in 56% yield from adenosine 3, involving a Mattocks bromoacetylation, a regio- and stereoselective ribo-epoxide ring opening with sodium azide and an efficient Staudin

Syntheses of puromycin from adenosine and 7-deazapuromycin from tubercidin, and biological comparisons of the 7-aza/deaza pair

Protection (05′) of 2′,3′-anhydroadenosine with tert-butyldiphenylsilyl chloride and epoxide opening with dimethylboron bromide gave the 3′-bromo-3′-deoxy xylo isomer which was treated with benzylisocyanate to give the 2′-O-(N-benzylcarbamoyl) derivative. Ring closure gave the oxazolidinone, and successive deprotection concluded an efficient route to 3′-amino-3′-deoxyadenosine. Analogous treatment ofthe antibiotic tubercidin {7-deazaadenosine; 4-amino-7-(β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidine} gave 3′-amino-3′-deoxytubercidin. Trifluoroacetylation of the 3′-amino function, elaboration of the heterocyclic amino group into a (1,2,4-triazol-4-yl) ring with N,N′-bis-[(dimethylamino)methylene]hydrazine, and nucleophilic aromatic substitution with dimethylamine gave puromycin aminonucleoside [9-(3-amino-3-deoxy-β-D-ribofuranosyl)-6-(dimethylamino)purine] and its 7-deaza analogue. Aminoacylation [BOC-(4-methoxy-L-phenylalanine)] and deprotection gave puromycin and 7-deazapuromycin. Most reactions gave high yields at or below ambient temperature. Equivalent inhibition of protein biosynthesis in a rabbit reticulocyte system and parallel growth inhibition of several bacteria were observed with the 7-aza/deaza pair. Replacement of N7 in the purine ring of puromycin by "CH" has no apparent effect on biological activity.