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Synthesis of labeled (10R)-Juvenile hormone III bisepoxide, and its photoaffinity analog, [12-3H]-(10R)-6,7,10,11-bisepoxyfarnesyl diazoacetate (BEFDA)

✍ Scribed by Bachir Latli; Glenn D. Prestwich


Publisher
John Wiley and Sons
Year
1991
Tongue
French
Weight
392 KB
Volume
29
Category
Article
ISSN
0022-2135

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✦ Synopsis


Abstract

Radiolabeled optically‐active JH III bisepoxide ([^3^H]‐(10__R__)‐JHB~3~) was synthesized from [12‐^3^H] (10__R__)‐JH III using dimethyldioxirane to give an inseparable mixture of diastereomers with the trans‐6,7‐epoxide syn or anti to the existing 10,11‐epoxide. [^3^H]‐(10__R__)‐JHB~3~ (or the unlabeled material) was converted in three steps to the corresponding (10__R__)‐6,7,10,11‐bisepoxyfarnesyl diazoacetate (BEFDA), a photoaffinity label for JHB~3~ receptors and binding proteins.