Facile synthesis of 9-[(1′R,2′S)-2′-hydroxy-3′-oxocyclopentan-1′-yl]-9-H-adenine possessing inhibitory activity against human recombinant S-adenosyl-l-homocysteine hydrolase

✍ Scribed by Yukio Kitade; Atushi Kozaki; Chizuko Yatome

• Book ID: 104211522
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 75 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01978-x

✦ Synopsis

Treatment of 4%-O-methanesulfonyl-2%,3%-O-isopropylidenenoraristeromycin with KOBu t gave the corresponding 3%,4%dehydro derivative, and subsequent deprotection resulted in the formation of 9-[(1%R,2%S)-2%-hydroxy-3%-oxocyclopentan-1%-yl]-9-Hadenine possessing inhibitory activity against human recombinant S-adenosyl-L-homocysteine hydrolase (EC 3.3.1.1). In sharp contrast to KOBu t , when lithium azide was adopted as a base, 9-[(1%R,2%S,3%R)-2%,3%-O-isopropylidenedioxy-4%-cyclopenten-1%-yl]-9-H-adenine was selectively obtained, and subsequent deprotection afforded DHCeA, which is a well-known potential antiviral agent.