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Synthesis of 2-amino-9-(3′-azido-2′,3′-dideoxy-beta-D-erythro-pentofuranosyl)-6-methoxy-9H-purine (AzddMAP) and AzddGuo

✍ Scribed by Merrick R. Almond; Jon L. Collins; Barbara E. Reitter; Janet L. Rideout; G.Andrew Freeman; Marty H. St Clair

Book ID: 104225898
Publisher: Elsevier Science
Year: 1991
Tongue: French
Weight: 271 KB
Volume: 32
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)93545-7

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✦ Synopsis

A novel synthesis of AzddMAP and AzddGuo is described starting from 1,

2-0-isopropylidene-alpha-D-xylofuranose. The key step in this synthesis involves the replacement of a diphenyl carbamoyl protecting group in the purine 6-position by methanol.

In 1987 Hartmann, Hunsmann, and Eckstein (1) reported that 3'-azido-2',3'-dideoxyguanosine, AzddGuo, inhibits the replication of human immunodeficiency virus in vitro. Eckstein et al. (2, 3) have reported that AzddGuo has a 50% effective antiviral dose against HIV in the range of 1.4 to 1.7 micromolar.

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