91432-48-3

Upstream product

• 103251-76-9 [(3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl sulfamate 
• 103251-77-0 N⁶-t-butyloxy-carbonyl-2-chloro-9-(2',3'-O-isopropylidene-5'-O-sulfamoyl-β-D-ribofuranosyl)adenine 
• 24639-06-3 ((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 110231-47-5 2-chloro-9-<2',3'-O-isopropylidene-5'-O-(N-t-butyloxycarbonyl-L-alanyl)sulfamoyl-β-D-ribofuranosyl>adenine 
• 103251-78-1 N⁶-t-butyloxycarbonyl-2-chloro-9-<2',3'-O-isopropylidene-5'-O-(N-t-butyloxycarbonyl-L-alanyl)sulfamoyl-β-D-ribofuranosyl>adenine 

Relevant academic research and scientific papers

A FACILE SYNTHESYS OF ASCAMYCIN AND RELATED ANALOGUES

The nucleoside antibiotic ascamycin (2-chloro-5'-O-(N-(L-alanyl)sulfamoyl)adenosine (1)) has been synthesized by an improved procedure involving the direct condensation of 2-chloro-2',3'-O-isopropylidene-5'-O-sulfamoyladenosine (3) with Boc-L-Ala-OSu in DMF and the presence of DBU, followed by removal of the protecting groups.A similar condensation of 3 with Boc-D-Ala-Osu and Boc-Gly-Osu, and subsequent deprotection, yielded the D-Ala and Gly analogues of 1, namely 2-chloro-5'-O-(N-(D-alanyl)sulfamoyl) and 2-chloro-5'-O-(N-(glycyl)sulfamoyl)adenosine (D-ascamycin (14) and (18)).Similar reactions of 2',3'-O-isopropylidene-5'-O-sulfamoyladenosine, (6) with the tree amino acid derivatives above mentioned provided the corresponding adenosine analogues 12,16, and 20.Several studies directed to demonstrate that the previous protection of the 6-NH2 group of the adenosine derivatives 3 and 6 is not necessary for the selective aminoacylation of the SO2NH2 group are also reported.