Synthesis of α1-(Cbz-aminoalkyl)-α2- (hydroxyalkyl)phosphinic esters

Tetrahedron Letters

Volumn 46, Issue 19, 2005, Pages 3359-3362

  Drag, Marcin ^a   Oleksyszyn, Józef ^a  

^a WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Addition; Phosphinates; Phosphinic esters

Indexed keywords

ACETIC ACID; ALDEHYDE; CHLOROTRIMETHYLSILANE; NITROGEN DERIVATIVE; PHOSPHINE DERIVATIVE;

ADDITION REACTION; ARTICLE; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 17144432219     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.083     Document Type: Article

References (17)

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11. 4) and evaporated in vacuo. Column chromatography on silica gel (70-200 mesh: 70 g) using hexane:AcOEt (1:1) gave the desired compound 5
12. 1H NMR data), which remained from the esterification of 3. Our attempts to eliminate this side product by several re-crystallizations from dichloromethane or hexane/AcOEt (1:1) and column chromatography were only partially successful
13. 31P NMR data). The susceptibility of these compounds to silylation and the stability of the silyl derivatives are unclear
14. +.
15. -1]) 1018.75 (s, P-OH), 1052.0 (s, C-O), 1161 (s, PO), 1613.9 (m, N-H), 2872.1-3026.8 (ms, C-H), 3183 (ms, O-H)
16. 13C NMR analysis. Our efforts to deprotect 5 in boiling 5 M HCl failed because of partial cleavage of the C-P bond
17. This work is the subject of patent applications-P370190 and P372057