5682-25-7

Basic information

• Product Name: 9-ALPHA-RIBOFURANOSYLADENINE
• Synonyms: 9-alpha-d-ribofuranosyl-9h-purin-6-amin;9-ALPHA-RIBOFURANOSYLADENINE;ALPHA-ADENOSINE;A-ADENOSINE FREE BASE;9-α-ribofuranosyladenine;9-α-Ribofuranosyladenine, 9-(α-D-Ribofuranosyl)adenine;alpha-D-Adenosine
• CAS NO: 5682-25-7
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 267.24
• Product Categories: Pharm intermediate
• Mol File: 5682-25-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 205-207 °C(lit.)
• Boiling Point: 676.3 °C at 760 mmHg
• Flash Point: 362.8 °C
• Appearance: /
• Density: 2.08 g/cm³
• Vapor Pressure: 5.07E-18mmHg at 25°C
• Refractive Index: 1.731
• Storage Temp.: −20°C
• CAS DataBase Reference: 9-ALPHA-RIBOFURANOSYLADENINE(CAS DataBase Reference)
• NIST Chemistry Reference: 9-ALPHA-RIBOFURANOSYLADENINE(5682-25-7)
• EPA Substance Registry System: 9-ALPHA-RIBOFURANOSYLADENINE(5682-25-7)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1 / PGIII
• Hazardous Substances Data: 5682-25-7(Hazardous Substances Data)

Usage

Uses

9-α-Adenosine is an intermediate in the proposed R&D synthesis of 2,3,5-Tri-O-acetyl α-Adenosine (T733805), an Adenosine (A280400(P)) impurity.

InChI:InChI=1/C24H16ClNO4S2/c1-29-20-13-15(7-12-19(20)30-23(28)16-8-10-17(25)11-9-16)14-21-22(27)26(24(31)32-21)18-5-3-2-4-6-18/h2-14H,1H3/b21-14+

Upstream product

• 201677-07-8 9-[2-deoxy-3,5-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-1-C-(2,2-dimethyl-1-oxopropoxy)-2-iodo-β-D-arabinofuranosyl]-9H-purin-6-amine 
• 58-61-7 adenosine 
• 902458-65-5 C₃₁H₂₅N₅O₇ 

Downstream Products

• 116163-47-4 endo-2',3'-O-(tert-butylmethylene)adenosine 
• 98145-34-7 endo-2',3'-O-isobutyleneadenosine 
• 16955-44-5 α-Adenosin-5'-phosphat 
• 953089-09-3 α-adenosine-2',3',5'-triacetate 

Relevant articles and documents

The rate of spontaneous cleavage of the glycosidic bond of adenosine

Previous estimates of the rate of spontaneous cleavage of the glycosidic bond of adenosine were determined by extrapolating the rates of the acid- and base-catalyzed reactions to neutral pH. Here we show that cleavage also proceeds through a pH-independent mechanism. Rate constants were determined as a function of temperature at pH 7 and a linear Arrhenius plot was constructed. Uncatalyzed cleavage occurs with a rate constant of 3.7 × 10-12 s-1 at 25 °C, and the rate enhancement generated by the corresponding glycoside hydrolase is ～5 × 1012-fold.

Generation and Characterization of Psoralen Radical Cations

Radical cations of psoralen, 8-methoxypsoralen (8-MOP) and 5-methoxypsoralen have been generated by photosensitized electron transfer in acetonitrile and aqueous buffer/acetonitrile (1:1) and have absorption maxima at 600, 650 and 550 nm, respectively. The radical cations have lifetimes of ～5 us under these conditions, are unreactive toward oxygen and show behavior typical of arylalkene radical cations in their reactivity toward nucleophiles and the precursor psoralens. Direct 355 nm excitation of 8-MOP in aqueous buffer at physiological pH results in monophotonic photoionization to give 8-MOP.+ with a quantum yield of 0.015. The 8-MOP.+ reacts with both guanosine and adenosine mononucleotides (k = 2.5 × 109 and 3.4 × 107 M-1 s-1, respectively) via electron transfer to give the purine radical cations, but does not react with pyrimidine mononucleotides. These results suggest that reactions of psoralen radical cations generated by electron transfer or photoionization may be involved in psoralen/UVA therapy.

Improved procedure for the regiospecific synthesis of 2'-deoxyribonucleosides

2'-Deoxyribonucleosides are regiospecifically synthesized in high yields by catalyzing with KI-dibenzo-18-crown-6 PTC the condensation between unprotected silylated purines and pyrimidines and the appropriate easily available 2-deoxy-ribofuranosyl or pyranosyl sugar derivatives.