Synthesis of 9-fluorenylmethoxycarbonyl-protected amino aldehydes

9-Fluorenylmethoxycarbonyl-protected amino aldehydes could be efficiently prepared in good yields by using two methods: (i) NaBH 4 reduction of Fmoc-protected mixed anhydrides, followed by the Swern oxidation of the alcohols; and (ii) LiAlH 4 reduction of Fmoc-protected amino acid Weinreb amides. Bo...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 9; no. 11; pp. 1855 - 1858
Main Authors Wen, James J, Crews, Craig M
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.06.1998
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
ALCOHOLS
RESIN
PROTECTED PEPTIDE-FRAGMENTS
SOLID-PHASE SYNTHESIS
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Summary:9-Fluorenylmethoxycarbonyl-protected amino aldehydes could be efficiently prepared in good yields by using two methods: (i) NaBH 4 reduction of Fmoc-protected mixed anhydrides, followed by the Swern oxidation of the alcohols; and (ii) LiAlH 4 reduction of Fmoc-protected amino acid Weinreb amides. Both methods afforded comparable overall synthetic yields (70–80%).
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(98)00183-9