52940-48-4

Basic information

• Product Name: 6-(morpholin-4-yl)-9-pentofuranosyl-9H-purine
• CAS NO: 52940-48-4
• Molecular Formula: C₁₄H₁₉N₅O₅
• Molecular Weight: 337.3312
• Mol File: 52940-48-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 684.9°C at 760 mmHg
• Flash Point: 368°C
• Density: 1.82g/cm³
• Vapor Pressure: 1.07E-19mmHg at 25°C
• Refractive Index: 1.805
• CAS DataBase Reference: 6-(morpholin-4-yl)-9-pentofuranosyl-9H-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(morpholin-4-yl)-9-pentofuranosyl-9H-purine(52940-48-4)
• EPA Substance Registry System: 6-(morpholin-4-yl)-9-pentofuranosyl-9H-purine(52940-48-4)

Safety Data

• Hazardous Substances Data: 52940-48-4(Hazardous Substances Data)

Upstream product

• 110-91-8 morpholine 
• 2004-06-0 6-Chloropurine riboside 
• 385806-18-8 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-(morpholin-4-yl)purine 
• 927818-53-9 O⁶-(benzotriazol-1-yl)inosine 
• 58-63-9 Inosine 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 

Relevant articles and documents

HFIP Promoted Low-Temperature SNAr of Chloroheteroarenes Using Thiols and Amines

A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base-free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.

O6-(benzotriazol-1-yl)inosine derivatives: Easily synthesized, reactive nucleosides (Journal of the American Chemical Society (2007) 129, (782-789))

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O6-(benzotriazol-1-yl)inosine derivatives: Easily synthesized, reactive nucleosides

A novel class of O6-(benzotriazol-1-yl)inosine as well as the corresponding 2′-deoxy derivatives can be conveniently prepared by a reaction between sugar-protected or -unprotected inosine or 2′- deoxyinosine nucleosides and 1H-benzotriazol-1-yloxy-tris(dimethylamino) phosphonium hexafluorophosphate (BOP). The reaction appears to proceed via a nucleoside phosphonium salt, and in the absence of any additional nucleophile, the released 1-hydroxybenzotriazole undergoes reaction with the formed phosphonium salt leading to the requisite O6-(benzotriazol-1-yl) inosine or 2′-deoxyinosine derivatives. Isolation and characterization of the phosphonium salt as well as analysis by 31P{1H} NMR appear to be consistent with this reaction pathway. The resulting O 6-(benzotriazol-1-yl)inosine derivatives are effective as electrophilic nucleosides, undergoing facile reactions with a variety of nucleophiles such as alcohols, phenols, amines, and a thiol. Unusual and challenging nucleoside derivatives such as an aryl-bridged dimer, a nucleoside-amino acid conjugate, and a nucleoside- nucleoside dimer have also been synthesized from the O6-(benzotriazol-1-yl)-2′- deoxyinosine derivative. Finally, a fully protected DNA building block, the O6-(benzotriazol-1-yl)-2′-deoxyinosine 5′-O-DMT 3′-O-phosphoramidite, has been prepared and a preliminary evaluation of its use for DNA modification has been performed. Results from these studies indicate several important facts: A single, simple methodological approach provides a class of stable, isolable ribo and 2′-deoxyribonucleoside derivatives that possess excellent reactivity for SNAr chemistry with a wide range of nucleophiles. Also, a benzotriazolyl nucleoside phosphoramidite appears to be a suitable reagent for incorporation into DNA for purposes of site-specific DNA modification.