3768-18-1Relevant articles and documents
A convenient synthesis of N4,O3′,O 5′-triacetyl-2′-ketocytidine
Kjell, Douglas P.,Slattery, Brian J.
, p. 469 - 474 (1997)
A convenient synthesis of the title compound in four steps from cytidine is reported. Key transformations include differentiation of the 2' position as N4,O3′,O5′ triacetyl-2,2′-anhydrocytidine, opening to the arabino derivative, and oxidation of the 2′ position with the Dess-Martin reagent. Copyright
Phosphonate analogues of cytosine arabinoside monophosphate
Chen, Xuemei,Jung, Kang-Yeoun,Wiemer, David F.,Wiemer, Andrew J.,Hohl, Raymond J.
, p. 1783 - 1786 (2002)
Phosphonate derivatives of cytidine and cytosine arabinoside have been prepared from the corresponding nucleoside aldehydes and tested for their ability to serve as substrates for nucleotide monophosphate kinase and for their toxicity to K562 leukemia cells.
Stereoselective synthesis of the 5′-hydroxy-5′-phosphonate derivatives of cytidine and cytosine arabinoside
Chen, Xuemei,Wiemer, Andrew J.,Hohl, Raymond J.,Wiemer, David F.
, p. 9331 - 9339 (2002)
Both the (R)- and (S)-5′-hydroxy 5′-phosphonate derivatives of cytidine and cytosine arabinoside (ara-C) have been prepared via phosphite addition or a Lewis acid mediated hydrophosphonylation of appropriately protected 5′-nucleoside aldehydes. Phosphite addition to a cytosine aldehyde protected as the 2′,3′-acetonide gave predominately the 5′R isomer, while phosphite addition to the corresponding 2′,3′-bis TBS derivative favored the 5′S stereochemistry. In contrast, phosphite addition to the 2′,3′-bis TBS protected aldehyde derived from ara-C gave only the 5′R adduct. However, TiC4-mediated hydrophosphonylation of the same ara-C aldehyde favored the 5′S stereoisomer by a 2:1 ratio. Once all four of the diastereomers were in hand, the stereochemistry of these compounds could be assigned based on their spectral data or that obtained from their O-methyl mandelate derivatives. After hydrolysis of the phosphonate esters and various protecting groups, the four α-hydroxy phosphonic acids were tested for their ability to serve as substrates for the enzyme nucleoside monophosphate kinase and for their toxicity to K562 cells.
SUBSTITUTED NUCLEOSIDE AND NUCLEOTIDE ANALOGS
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Page/Page column 138, (2010/10/03)
Disclosed herein are nucleotide analogs with protected phosphates, methods of synthesizing nucleotide analogs with protected phosphates and methods of treating diseases and/or conditions such as viral infections, cancer, and/or parasitic diseases with the nucleotide analogs with protected phosphates.
Electron-deficient benzotriazoles for the selective N-acetylation of nucleosides
Reid, Andrew K.,McHugh, Callum J.,Richie, Graham,Graham, Duncan
, p. 4201 - 4203 (2007/10/03)
The use of an acetylated benzotriazole for the selective protection of the amino groups of cytidine and 2′-deoxycytidine is reported. The use of the acetyl group is of considerable interest industrially in this role, and a single-step protection strategy advantageous in bulk production. 1-Acetyl-4-nitrobenzotriazole was found to readily acetylate the amine of cytidine preferentially over the exposed alcohol functionalities. With adaptation of the protocol, 2′-deoxycytidine was protected using the same reagent. A similar approach was attempted for the benzoylation of adenosine but was found to be unsuitable.
