Asymmetric synthesis of N‐protected chiral 1‐aminoalkylphosphonic acids and synthesis of side chain–functionalized depsiphosphonopeptides

Optically active 1‐aminoalkylphosphonic acid derivatives were synthesized in moderate yields and optical purities via Mannich‐type reactions of benzyl carbamate, aldehydes, and optically pure chlorophosphites. Side chain–functionalized depsiphosphonopeptides were also prepared in satisfactory yields directly from one‐pot reactions of benzyl carbamate, aldehydes, and diethyl (R,R)‐2‐chloro‐1,3,2‐dioxaphospholane‐4,5‐dicarboxylate. Copyright © 2005 European Peptide Society and John Wiley & Sons, Ltd.

[1]  K. Swamy,et al.  Cyclic chlorophosphites as scaffolds for the one-pot synthesis of α-aminophosphonates under solvent-free conditions , 2005 .

[2]  A. Chan,et al.  An efficient chiral phosphorus derivatizing agent for the determination of the enantiomeric excess of chiral alcohols and amines by 31P NMR spectroscopy , 2002 .

[3]  Jiaxi Xu,et al.  A CONVENIENT METHOD FOR THE SYNTHESIS OF N-PROTECTED 1-AMINOALKYLPHOSPHONATE MIXED MONOTHIOESTERS AND DITHIOESTERS , 2001 .

[4]  Jiaxi Xu,et al.  A novel and convenient method for synthesizing unsymmetrical N-benzyloxycarbonyl-protected 1-amino-1-arylalkylphosphonate mixed diesters , 2001 .

[5]  P. Kafarski,et al.  Synthesis of Phosphono‐ and Phosphinopeptides , 2000 .

[6]  Jiaxi Xu,et al.  A Facile Synthesis of N-Protected 1-Aminoalkylphosphonamidate Derivatives , 2000 .

[7]  Jiaxi Xu,et al.  A novel synthetic route to N-protected 1-aminoalkylphosphonates , 2000 .

[8]  Ruyu Chen,et al.  Synthesis of 2-[(Benzyloxycarbonylamino)phenylmethyl]-1,3,2-benzodioxaphosphole 2-Oxides , 1998 .

[9]  Q. Dai,et al.  A Modified Method for Synthesis of Alkyl Hydrogen α-(Benzyloxycarbonylamino)-benzylphosphonates , 1997 .

[10]  Q. Dai,et al.  A Facile Synthesis of Phenyl Hydrogen α-(Benzyloxycarbonylamino)benzylphosphonates , 1997 .

[11]  Carol M. Taylor,et al.  Enantioselective Synthesis of Diverse .alpha.-Amino Phosphonate Diesters , 1995 .

[12]  Yen-Hsiang Liu,et al.  Synthesis of Phosphonate and Thiophosphonate Esters and Amides from Hydrogen-Phosphinates by a Novel One-Pot Activation-Coupling-Oxidation Procedure , 1995 .

[13]  P. Jouin,et al.  (1H-Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium Hexafluorophosphate- and (1H-Benzotriazol-1-yloxy)tripyrrolidinophosphonium Hexafluorophosphate-Mediated Activation of Monophosphonate Esters: Synthesis of Mixed Phosphonate Diesters, the Reactivity of the Benzotriazolyl Phosphonic Esters vs th , 1995 .

[14]  J. Brunel,et al.  The use of (4r,5r)-dicarboalkoxy 2-chloro 1,3,2-dioxaphospholanes as new chiral derivatizing agents for the determination of enantiomeric purity of alcohols by 31P NMR. , 1992 .

[15]  C. Yuan,et al.  Studies on Organophosphorus Compounds; XLI. A Convenient Synthesis of Alkyl Hydrogen α-(Benzyloxycarbonylamino)benzylphosphonates , 1990 .

[16]  M. Hoffmann.  A Convenient Synthesis of Alkyl Hydrogen 1-(Benzyloxycarbonylamino)-alkanephosphonates , 1986 .

[17]  P. Bartlett,et al.  Inhibition of chymotrypsin by phosphonate and phosphonamidate peptide analogs , 1986 .