000158132 001__ 158132
000158132 005__ 20180913060134.0
000158132 037__ $$aARTICLE
000158132 245__ $$aAsymmetric synthesis of orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine
000158132 269__ $$a2003
000158132 260__ $$c2003
000158132 336__ $$aJournal Articles
000158132 500__ $$aCAN 140:16939
000158132 500__ $$a34-2
000158132 500__ $$aAmino Acids, Peptides, and Proteins
000158132 500__ $$aInstitut de Chimie des Substances Naturelles, CNRS,Gif-sur-Yvette,Fr.
000158132 500__ $$aJournal
000158132 500__ $$a0936-5214
000158132 500__ $$awritten in English.
000158132 500__ $$a61278-21-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (N-protection; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 1643-19-2 (Tetrabutylammonium bromide); 200132-54-3; 219601-70-4; 534570-50-8 Role: CAT (Catalyst use), USES (Uses) (asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 630400-90-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 329912-53-0P; 371972-14-4P; 630400-89-4P Role: SPN (Synthetic preparation), PREP (Preparation) (asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 23788-74-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (azidation; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 81477-94-3 Role: RCT (Reactant), RACT (Reactant or reagent) (coupling with (iodomethyl)oxazolidine; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 630400-88-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (coupling with imino ester; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 630400-87-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (iodination; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 135582-93-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (monotosylation; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 630400-86-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (oxazolidine ring closure; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 85820-82-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (redn./ring opening; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); 13139-17-8; 22323-82-6 Role: RCT (Reactant), RACT (Reactant or reagent) (tosylation; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.)
000158132 520__ $$aSynthesis of orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithines I is reported featuring an asym. alkylation of N-(diphenylmethylene)glycine tert-Bu ester with (5S)-N-benzyloxycarbonyl-5-iodomethyl oxazolidine. Double stereoselection was examd. using chiral ammonium salts as phase transfer catalysts, and a substrate-directed chiral induction is documented. [on SciFinder (R)]
000158132 6531_ $$aAsymmetric synthesis and induction (asym. synthesis of orthogonally protected hydroxyornithines and their derivs.); Amino acids Role: SPN (Synthetic preparation)
000158132 6531_ $$aPREP (Preparation) (esters; asym. synthesis of orthogonally protected hydroxyornithines and their derivs.)
000158132 6531_ $$aornithine hydroxy orthogonally protected asym synthesis
000158132 700__ $$aLepine, Renaud
000158132 700__ $$aCarbonnelle, Anny-Claude
000158132 700__ $$0244710$$aZhu, Jieping$$g206332
000158132 773__ $$k10$$q1455-1458$$tSynlett
000158132 909C0 $$0252341$$pLSPN$$xU12326
000158132 909CO $$ooai:infoscience.tind.io:158132$$pSB$$particle
000158132 937__ $$aEPFL-ARTICLE-158132
000158132 973__ $$aOTHER$$rREVIEWED$$sPUBLISHED
000158132 980__ $$aARTICLE