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Asymmetric synthesis of erythro-β-hydroxyasparagine

✍ Scribed by Douglas Wong; Carol M. Taylor

Book ID
104096154
Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
323 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

erythro-Hydroxyasparagine (eHyAsn, 1) occurs in a number of naturally occurring peptides and proteins. Previous syntheses have relied on enzyme-catalyzed reactions to produce relevant, optically active intermediates. We report herein a completely chemical synthesis that intercepts Boger's synthesis of the diastereomer (tHyAsn, 4), utilizing a Sharpless asymmetric aminohydroxylation reaction to introduce the two stereocenters. Boc-HyAsn(OTBS)-OH (10) was coupled effectively with phenylalanine methyl ester using EDC/HOBt.

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✍ Ulrich Groth; Ulrich Schöllkopf; Thomas Tiller 📂 Article 📅 1991 🏛 Elsevier Science 🌐 French ⚖ 511 KB

D-erythro-Sphingosine 9 is a building block of cerebrosides and glycosphingolipids and was synthesized in 5 steps via an asymmetric aldol addition of the lithiated bislactim ether of cyclo-(L-Val-Gly) 4 to (2E)-hexadecenal(3) in an overall yield of 21 %. I.