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Synthesis of Fmoc-protected (2S,3S)-2-hydroxy-3-amino acids from a furyl substituted chiral cyanohydrin

✍ Scribed by Reynier A. Tromp; Michael van der Hoeven; Alessia Amore; Johannes Brussee; Mark Overhand; Gijs A. van der Marel; Arne van der Gen

Book ID: 104359792
Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 210 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00218-0

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✦ Synopsis

A stereoselective chemoenzymatic synthesis of Fmoc-protected (2S,3S)-2-hydroxy-3-amino acids 6 is described. After the formation of cyanohydrin 2 from 2-furaldehyde in the presence of R-oxynitrilase and subsequent protection, 3 was transformed into fully protected ethanolamines 5. Ozonolysis provided the target compounds in good yields.

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