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The synthesis of (5R)- and (5S)-[5-3H]-L-ornithine

✍ Scribed by Ronald J. Parry; Shyhchen Ju; Bill J. Baker


Book ID
102901145
Publisher
John Wiley and Sons
Year
1991
Tongue
French
Weight
507 KB
Volume
29
Category
Article
ISSN
0022-2135

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✦ Synopsis


A practical synthesis of (5R)and (5S)-[5-3H]-L-ornithine is described. The key steps in the synthesis are the reduction of vonnyl-3H]J-hexenal with S-or R-Alpine Borane to (1R)and (1s)-[ 1-3H]J-hexen-l-ol and the use of the Evans electrophilic azidation of c h i d h i d e enolates to introduce the a-amino group of ornithine. The stereochemistry expected for the Alpine Borane reduction was v d i e d by NMR analysis of the camphanate ester derived from reduction of vomyf-2H]-S-hexenal with R-Alpine Borane.


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