28070-06-6Relevant academic research and scientific papers
A Click-Chemistry Linked 2′3′-cGAMP Analogue
Dialer, Clemens Reto,Stazzoni, Samuele,Drexler, David Jan,Müller, Felix Moritz,Veth, Simon,Pichler, Alexander,Okamura, Hidenori,Witte, Gregor,Hopfner, Karl-Peter,Carell, Thomas
, p. 2089 - 2095 (2019)
2′3′-cGAMP is an uncanonical cyclic dinucleotide where one A and one G base are connected via a 3′-5′ and a unique 2′-5′ linkage. The molecule is produced by the cyclase cGAS in response to cytosolic DNA binding. cGAMP activates STING and hence one of the most powerful pathways of innate immunity. cGAMP analogues with uncharged linkages that feature better cellular penetrability are currently highly desired. Here, the synthesis of a cGAMP analogue with one amide and one triazole linkage is reported. The molecule is best prepared via a first CuI-catalyzed click reaction, which establishes the triazole, while the cyclization is achieved by macrolactamization.
Selective preparation of 6- and 7-(polyhydroxypropyl)-pterins from pentos-2-uloses
Hanaya, Tadashi,Ito, Kasumi
, p. 1491 - 1499 (2014)
The Gabriel-Isay condensation of three types of pentos-2-uloses with 2,5,6-triaminopyrimidin-4(3H)-one (3) was examined under both acidic and basic conditions. The condensation of 5-deoxy- and 5-O-protected pentofuranos-2-uloses with 3 at pH 8 afforded 6-
A convergent total synthesis of hemibrevetoxin B
Zakarian, Armen,Batch, Alexandre,Holton, Robert A.
, p. 7822 - 7824 (2007/10/03)
A convergent biomimetic synthesis of hemibrevetoxin B from d-glucal and d-arabinose utilizes an electrophile-promoted cascade anti-Baldwin cyclization of an epoxy alcohol. The epoxy alcohol arises from a palladium-catalyzed coupling of a highly functionalized organozinc compound and an alkenyl iodide, which serve as two chiral building blocks of similar size and complexity. This first successful implementation of a cascade epoxy alcohol cyclization for the synthesis of marine polycyclic ether toxins proceeds in 39 steps and 4% overall yield. Copyright
Synthesis of a diazasugar with nitrogen in place of the anomeric carbon and glycosidic oxygen
S?hoel, Helmer,Liang, Xifu,Bols, Mikael
, p. 347 - 348 (2007/10/03)
A D-galactose analogue with a hydrazine in place of C-1 was synthesised.
A CONCISE SYNTHESIS OF PATULIN FROM ARABINOSE
Gill, G. Bryon,Pattenden, Gerald,Stapleton, Alan
, p. 2875 - 2878 (2007/10/02)
Conversion of arabinose (5) to the protected ketone (7), followed by Wittig condensation to (9), acid catalysed cyclisation (to 10), and dehydration, provides a brief synthesis of the fungal metabolite patulin (1), produced by Penicillium and Aspergilius
REGIOSPECIFIC SYNTHESIS OF 2'-DEOXY-2',2''-DIDEUTERIO NUCLEOSIDES
Wu, J-C.,Bazin, H.,Chattopadhyaya, J.
, p. 2355 - 2368 (2007/10/02)
Two routes have been devised for the first synthesis of 2',2''-dideuterio-2'-deoxynucleosides.First route involves the oxidation of an appropriately 3',5'-protected ribonucleosides with CrO3-pyridine-acetic anhydride complex, followed by direct
