Large scale syntheses of N-protected 2,3-methanomethionine stereoisomers Academic Article

abstract

• Three stereoisomers of N-protected forms of 2,3-methanomethionine (cyclopropyl derivatives of methionine, or "cyclo-Met") were prepared. Two of the syntheses developed involved diol (S)-1, which was more easily obtained from L-gulono-1,4-lactone than via juxtaposition of the benzyl protection of (A)-1. The cis-cyclo-Met derivative (cis refers to the orientation of the side chain relative to the amino functionality), FMOC-(2R,3S)-cyclo-Met, was obtained via a route based on a previous synthesis of (2R,3S)-cyclo-Met from the lactone 3, but the protected trans-cyclo-Met, BOC-(2S,3S)-cyclo-Met, was obtained via an improved procedure that does not involved lactone 3.

authors

• Burgess, Kevin

published proceedings

• SYNTHESIS-STUTTGART

altmetric score

• 3

author list (cited authors)

• Burgess, K., & Ke, C. Y.

citation count

• 21

complete list of authors

• Burgess, K||Ke, CY

publication date

• December 1996

publisher

• Thieme  Publisher

published in

• Synthesis  Journal

keywords

• 15 Life On Land

Digital Object Identifier (DOI)

• 10.1055/s-1996-4425

start page

• 1463

end page

• &

volume

• 1996

issue

• 12

URL

• http://dx.doi.org/10.1055/s-1996-4425

user-defined tag

• 15 Life on Land