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Title: Diastereoselective conversion of l-(s)-erythrulose to 2-amino-2-deoxy-l-erythritol
Authors: Dequeker, Elisabeth ×
Compernolle, Frans
Toppet, Suzanne
Hoornaert, Georges #
Issue Date: Jan-1995
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:51 issue:20 pages:5877-5890
Abstract: L-(S)-Erythrulose (1) was converted into 2-amino-2-deoxy-L-erythritol (2) (six steps, overall yield 35%) through diastereoselective reduction of the bridged orthoester 21, (1S,5S)-2,7,8-trioxabicyclo[3.2.l]octan-4-one-O-benzyloxime, with K-selectride(R) as the key process. Alternative methods, involving reduction of the imino group in acyclic O-benzyloxime derivatives of 1, or reductive amination of the 2-ketone function, afforded various proportions of erythro and threo 2-amino diastereoisomers. The distribution of rotamers for the deprotected ammonium salts apparently is governed by hydrogen bonding between the ammonium group and the 3-hydroxyl oxygen, resulting in characteristic (3)J(H-2,H-3) coupling constant values. Substitution of the bridged O-benzyloximes 21 and 22 via deprotonation of the alpha-methylene position was not successful.
URI: 
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
Chemistry - miscellaneous
Human Mutations and Polymorphisms Section (-)
Biomedical Quality Assurance Research Unit
× corresponding author
# (joint) last author

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