150575-74-9Relevant articles and documents
Synthesis of a Threosyl-C-nucleoside Phosphonate
Nie, Peng,Groaz, Elisabetta,Herdewijn, Piet
, p. 6666 - 6672 (2019)
A general synthetic route for the preparation of the first analogue of a new series of sugar-modified C-nucleoside phosphonates is detailed. Such derivative contains a four-carbon l-threose sugar moiety substituted with a phosphonomethoxy group at the 3′-position and pyrrolo[2,1-f][1,2,4]triazin-4-amine as nucleobase. A C-nucleoside was initially prepared by coupling a benzyl protected l-threono-1,4-lactone intermediate with the corresponding aglycon moiety. The choice of a tert-butyldiphenylsilyl group was found to be crucial to achieve the regioselective protection of the hydroxyl group at the 3′-position. Moreover, it allowed to smoothly perform further synthetic manipulations, including the introduction of a benzyl protected phosphonate synthon under basic conditions, which eventually led to the desired compound after final deprotection.
Synthesis of glycaro-1,5-lactams and tetrahydrotetrazolopyridine-5- carboxylates: Inhibitors of β-D-glucuronidase and α-L-iduronidase
Pabba, Jagadish,Rempel, Brian P.,Withers, Stephen G.,Vasella, Andrea
, p. 635 - 666 (2007/10/03)
The known glucaro-1,5-lactam 8, its diastereoisomers 9-11, and the tetrahydrotetrazolopyridine-5-carboxylates 12-14 were synthesised as potential inhibitors of β-D-glucuronidases and α-L-iduronidases. The known 2,3-di-O-benzyl-4,6-O-benzylidene-D-galactos
