274905-53-2Relevant articles and documents
Addressing regio- And stereo-specificity challenges in the synthesis of nucleoside 2′,3′-cyclic monophosphate analogs-a rapid and facile synthesis of nucleoside-2′,3′-: O, O -phosphoro-thioate or -selenoate, and elucidation of the origin of the rare specificity
Nassir, Molhm,Balaom, Lara,Fischer, Bilha
, p. 11633 - 11636 (2020/10/19)
A new facile, rapid, stereo- and regio-selective one-pot synthesis of nucleoside-2′,3′-O,O-phosphorothioate and selenoate analogs has been developed. This method avoids the need for protection strategies and chiral reagents, chiral metal catalysts, or chiral separations. This synthetic method has been applied to all natural nucleosides (U/A/G/C/T). Furthermore, we have deciphered the origin of the stereo- and regio-selectivity of the reaction.
Synthesis and separation of diastereomers of uridine 2′,3′-cyclic boranophosphate
He, Kaizhang,Shaw, Barbara Ramsay
, p. 615 - 617 (2007/10/03)
The first boron-containing 2′,3′-cyclic phosphate-modified analogue, uridine 2′,3′-cyclic boranophosphate (2′,3′-cyclic-UMPB), was synthesized. 5′-O-Protected uridine was cyclophosphorylated by diphenyl H-phosphonate to yield uridine 2′,3′-cyclic H-phosphonate, which upon silylation followed by boronation and subsequent acid treatment gave 2′,3′-cyclic-UMPB in high yield. The two diastereomers of 2′,3′-cyclic-UMPB were separated by HPLC. An alternative method for synthesis of uridine 2′,3′-cyclic phosphorothioate (2′,3′-cyclic-UMPS) via H-phosphonate was also described.
