Process research of (R)-cyclohexyl lactic acid and related building blocks: a comparative study

…, PF Fauquex, P Marschal, WU Lottenbach…

Index: Storz, Thomas; Dittmar, Peter; Fauquex, Pierre Francois; Marschal, Philippe; Lottenbach, Willy Urs; Steiner, Heinz Organic Process Research and Development, 2003 , vol. 7, # 4 p. 559 - 570

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Citation Number: 27

Abstract

(S)-Cyclohexyl lactic acid is a component of the selective E-selectin inhibitor 2 ((S)-cHexLact- 2-O-(3-Galβ (1→ 3) ddGlc (4→ 1) αFuc). We describe the evaluation of various synthetic routes to this building block:(A) diazotation of phenylalanine followed by phenyl ring hydrogenation;(B) phenyl ring hydrogenation of phenyl alanine followed by diazotation;(C) acidic hydrolysis of the cyanohydrin derived from phenylacetaldehyde, enantiomeric ...