Improved synthesis of (R)-glycine-d-N-15

Citation
Jr. Walker et Rw. Curley, Improved synthesis of (R)-glycine-d-N-15, TETRAHEDRON, 57(31), 2001, pp. 6695-6701
Citations number
45
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
31
Year of publication
2001
Pages
6695 - 6701
Database
ISI
SICI code
0040-4020(20010730)57:31<6695:ISO(>2.0.ZU;2-R
Abstract
Previously, we have synthesized the title glycine to permit assignment of t he prochiral alpha -protons of glycine residues in the NMR study of the pro tein FKBP. A key, and low yielding step in this synthesis occurs in the rut henium tetraoxide mediated degradation of N-t-Boc-p-methoxybenzyl amine to N-t-Boc-glycine. Efforts to improve this key step by exploring different su bstrates and N-protecting groups were successful to render this synthesis a menable for the large scale production of (R)-glycine-d-N-15. (C) 2001 Else vier Science Ltd. Ail rights reserved.