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Enantiospecific synthesis of the immunopotentiators erythro-9 (2-hydroxy-3-nonyl) hypoxanthines and the threo-diastereomers.

โœ Scribed by M. Bessodes; E. Abushanad; K. Antonakis

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
207 KB
Volume
25
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The title compounds were prepared enantiospecifically by kinetic resolution of I+/-) 1-nonene-301 via Sharpless oxidation. The products 1,2R-epoxy-nonane-3S-01 and 1-nonene-3R-ol were efficiently converted to all four stereoisomers of 2-hydroxy-3-nonylamine, which were subsequently incorporated into the target hypoxanthines to evaluate their immunopotentiating activity. (+/-I Erythro-9(2-hydroxy-3-nonyl) hypoxanthine (l_, NPT 15392) has been reported to have immunopotentiating activity'. This compound is structurally related to the adenine analog 2 (EHNA), which is a potent inhibitor of adenosine deaminase2, and has antiviral activity in vitro3. It was recently shown4'5 that chirality in the

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โœ Toshio Sato; Kazuhisa Tajima; Tamotsu Fujisawa ๐Ÿ“‚ Article ๐Ÿ“… 1983 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 148 KB

The ester enolate Claisen rearrangement of IE)-and IZ)-2-butenyl ## 2-hydroxyacetates gave erythro-and threo-2-hydroxy-3-methyl-4-pentenoic acids with high diastereoselectivity via silyl ketene acetals, respect<vely.