493039-13-7

Upstream product

• 493039-05-7 dimethyl (3R)-3-[N-(9-phenyl-9-fluorenyl)amino]adipate 
• 493039-11-5 (1R,2S,4R)-4-[N-(9-phenyl-9-fluorenyl)amino]-2-hydroxycyclopentanemethanol 
• 493039-07-9 methyl (1RS,2RS,4R)-2-hydroxy-4-[N-(9-phenyl-9-fluorenyl)amino]cyclopentanecarboxylate 
• 493039-06-8 methyl (1RS,4R)-2-oxo-4-[N-(9-phenyl-9-fluorenyl)amino]cyclopentanecarboxylate 
• 493039-10-4 (1S)-1-[N-(9-phenyl-9-fluorenyl)amino]-3-(hydroxymethyl)-cyclopentene 
• 493039-08-0 methyl (4S)-4-[N-(9-phenyl-9-fluorenyl)amino]-1-cyclopentenecarboxylate 
• 98-88-4 benzoyl chloride 

Downstream Products

• 493039-15-9 (8R)-3-[(1S,2R,4R)-2-(benzoyloxymethyl)-1-benzoyloxycyclopent-4-yl]-8-[(tert-butyldimethylsilyl)oxy]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine 

Relevant academic research and scientific papers

Enantiospecific synthesis of carbapentostatins

In this paper we describe enantioselective syntheses of (+)-carbapentostatin (8) and its cyclopentyl analogue 12b. A new and efficient one-pot, two-step preparation of aldehyde 15 has been developed, based on the borane reduction of N-Pf-protected L-aspartic acid γ-methyl ester (13) and Swern oxidation of the resulting alcohol. Homologation to diester 18 and ring formation by Dieckman cyclization, followed by reduction and dehydration steps, afford the 4-amino-1-cyclopentenemethanol derivative 22. Hydroboration and oxidation transform this compound stereospecifically into aminocyclopentanol 26, the key aminocyclitol component for an asymmetric synthesis of (+)- carbapentostatin.