Synthesis of Amphiphilic Amino Alcohols

REFERENCES

• Ager , D. J. ; Prakash , I. ; Schaad , D. R. 1,2-Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis . Chem. Rev. 1996 , 96 , 835 – 876 .
   PubMed Web of Science ®Google Scholar
• Winsor , P. A. Binary and multicomponent solutions of amphiphilic compounds: Solubilization and the formation, structure, and theoretical significance of liquid crystalline solutions . Chem. Rev. 1968 , 68 , 1 – 40 .
   Web of Science ®Google Scholar
• (a) Hepworth , P. Non-ionic surfactants . In Chemistry and Technology of Surfactants ; R. Farm (Ed.); Blackwell Publishing Ltd : Oxford , UK , 2006 ; chapter 5 ; (b) Holmberg , K. ; Jonsson , B. ; Kronberg , B. ; Lindman , B. Surfactants and Polymers in Aqueous Solution, , 2nd ed. ; Wiley & Sons : Chichester , England , 2003 ; pp. 1 – 37 .
   Google Scholar
• (a) Taveira , A. F. ; Hyaric , M. L. ; Reis , E. F. C. ; Araujo , D. P. ; Ferreira , A. P. ; de Souza , M. A. ; Alves , L. L. ; Lourenco , M. C. S. ; Vicente , F. R. C. ; de Almeida , M. V. Preparation and antitubercular activities of alkylated amino alcohols and their glycosylated derivatives . Bioorg. Med. Chem. 2007 , 15 , 7789 – 7794 ; (b) Tewari , N. ; Tiwari , V. K. ; Tripathi , R. P. ; Chaturvedi , V. ; Srivastava , A. ; Srivastava , R. ; Shukla , P. K. ; Chaturvedi , A. K. ; Gaikwad , A. ; Sinha , S. ; Srivastava , B. S. Synthesis of galactopyranosyl amino alcohols as a new class of antitubercular and antifungal agents . Bioorg. Med. Chem. Lett. 2004 , 14 , 329 – 332 .
   Google Scholar
• Spichiger-Keller , U. E. Ionophores, ligands, and reactands. Anal. Chim. Acta 1999, 400, 65–72.
   Google Scholar
• World Health Organization . Treatment of Tuberculosis: Guidelines for National Programmes ; 2003 . Available at http://whqlibdoc.who.int/hq/2003/WHO_CDS_TB_2003.313_eng.pdf.
   Google Scholar
• Yendapally , R. ; Lee , R. E. Design, synthesis, and evaluation of novel ethambutol analogues . Bioorg. Med. Chem. Lett. 2008 , 18 , 1607 – 1611 .
   Google Scholar
• Tripathi , R. P. ; Tripathi , R. ; Tiwari , V. K. ; Bala , L. ; Sinha , S. ; Srivastava , A. ; Srivastava , R. ; Srivastava , B. S. Synthesis of glycosylated β-amino acids as new class of antitubercular agents . Eur. J. Med. Chem. 2002 , 37 , 773 .
   PubMed Web of Science ®Google Scholar
• Tewari , N. ; Tiwari , V. K. ; Tripathi , R. P. ; Chaturvedi , V. ; Srivastava , A. ; Srivastava , R. ; Shukla , P. K. ; Chaturvedi , A. K. ; Gaikwad , A. ; Sinha , S. ; Srivastava , B. S. Synthesis of galactopyranosyl amino alcohols as a new class of antitubercular and antifungal agents . Bioorg. Med. Chem. Lett. 2004 , 14 , 329 – 332 .
   Google Scholar
• de Almeida , M. V. ; Le Hyaric , M. ; Amarante , G. W. ; Silva Lourenco , M. C. ; Lima Brandao , M. L. Synthesis of amphiphilic galactopyranosyl diamines and amino alcohols as antitubercular agents . Eur. J. Med. Chem. 2007 , 42 , 1076 – 1083 , and references therein .
   Google Scholar
• Bermejo , A. ; Figadère , B. ; Zafra-Polo , M. C. ; Barrachina , I. ; Estornell , E. ; Cortes , D. Acetogenins from Annonaceae: Recent progress in isolation, synthesis, and mechanisms of action . Nat. Prod. Rep. 2005 , 22 , 269 – 303 .
   PubMed Web of Science ®Google Scholar
• (a) Wang , M. ; Shen , J. Synthesis of simplified analogue of acetogenin bearing N,N′-dibenzyl ethylenediamine moiety . Chin. J. Synth. Chem. 2006 , 14 , 337 – 341 ; (b) Wang , M. ; Chen , Y. ; Lou , L. ; Tang , W. ; Wang , X. ; Shen , J. Synthesis of pyrrolidine analogues of solamin . Tetrahedron Lett. 2005 , 46 , 5309 – 5312 .
   Google Scholar
• (a) Larrow , J. F. ; Schaus , S. E. ; Jacobsen , E. N. Kinetic resolution of terminal epoxides via highly regioselective and enantioselective ring opening with TMSN3: An efficient, catalytic route to 1,2-amino alcohols . J. Am. Chem. Soc. 1996 , 118 , 7420 – 7421 ; (b) Olofsson , B. ; Khamrai , U. ; Somfai , P. A regio- and stereodivergent synthesis of vic-amino alcohols . Org. Lett. 2000 , 2 , 4087 – 4089 ; (c) Sekar , G. ; Singh , V. K. An efficient method for cleavage of epoxides with aromatic amines . J. Org. Chem. 1999 , 64 , 287 – 289 .
   Web of Science ®Google Scholar
• (a) Adolfsson , H. ; Balan , D. Metal-catalyzed synthesis of epoxides ; In Aziridines and Epoxides in Organic Synthesis ; A. Yudin (Ed.); Wiley-VCH : Weinheim , Germany , 2006 ; pp. 185 – 228 ; (b) Jacobsen, E. N. Asymmetric catalytic epoxidation of unfunctionalized olefins; In Catalytic Asymmetric Synthesis; I. Ojima (Ed.); VCH: New York, 1993; pp. 159–202; (c) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Catalytic asymmetric dihydroxylation. Chem. Rev. 1994, 94, 2483–2547.
   Google Scholar
• (a) See Möller , F. Methoden der Organische Chemie (Houben-Weyl), , 4th ed.; E. Müller (Ed.); Thieme Verlag : Stuttgart , 1957 ; vol. 11/1, pp. 311–326; (b) Mousseron, M.; Jullien, J.; Jolchine, Y. Alicyclic series, XXXIV: Preparation and properties of substituted amines. Bull. Soc. Chim. Fr. 1952, 757–766; (c) Chini, M.; Crotti, P.; Macchia, F. Regioalternating selectivity in the metal salt catalyzed aminolysis of styrene oxide. J. Org. Chem. 1991, 56, 5939–5942; (d) Caron, M.; Sharpless, K. B. Titanium isopropoxide–mediated nucleophilic openings of 2,3-epoxy alcohols: A mild procedure for regioselective ring-opening. J. Org. Chem. 1985, 50, 1557–1560.
   Google Scholar
• Crispino , G. A. ; Jeong , K. S. ; Kolb , H. C. ; Wang , Z. M. ; Xu , D. ; Sharpless , K. B. Improved enantioselectivity in asymmetric dihydroxylations of terminal olefins using pyrimidine ligands . J. Org. Chem. 1993 , 58 , 3785 – 3786 .
   Google Scholar
• Martinelli , M. J. ; Nayyar , N. K. ; Moher , E. D. ; Dhokte , U. P. ; Pawlak , J. M. ; Vaidyanathan , R. Dibutyltin oxide catalyzed selective sulfonylation of α-chelatable primary alcohols . Org. Lett. 1999 , 1 , 447 – 450 .
   Web of Science ®Google Scholar
• Foglia , T. A. ; Swern , D. Pseudo-halogens. VII. New synthesis of aziridines and oxazolidones . J. Org. Chem. 1967 , 32 , 75 – 78 .
   Google Scholar
• Lupi , V. ; Albanese , D. ; Landini , D. ; Scaletti , D. ; Penso , M. Synthesis of 2,6-disubstituted morpholines through regioselective oxiranes ring opening by tosylamide under PTC conditions . Tetrahedron 2004 , 60 , 11709 – 11718 .
   Google Scholar
• (a) Fukuyama , T. ; Jow , C.-K. ; Cheung , M. 2- and 4-Nitrobenzenesulfonamides: Exceptionally versatile means for preparation of secondary amines and protection of amines . Tetrahedron Lett. 1995 , 36 , 6373 – 6374 ; (b) Kan , T. ; Fukuyama , T. Ns strategies: A highly versatile synthetic method for amines . Chem. Comm. 2004 , 353 – 359 .
   Web of Science ®Google Scholar
• Zeng , B.-B. ; Wu , Y. ; Jiang , S. ; Yu , Q. ; Yao , Z.-J. ; Liu , Z.-H. ; Li , H.-Y. ; Li , Y. ; Chen , X.-G. ; Wu , Y.-L. Studies on mimicry of naturally occurring annonaceous acetogenins: Non-THF analogues leading to remarkable selective cytotoxicity against human tumor cells . Chem. Eur. J. 2003 , 9 , 282 – 290 .
   Google Scholar
• Chen , C. S. ; Liu , Y. C. A chemoenzymatic access to optically active 1,2-epoxides . Tetrahedron Lett. 1989 , 30 , 7165 – 7168 .
   Google Scholar
• Altinis Kiraz , C. I. ; Mora , L. ; Jimenez , L. S. Oxidation of alkenes by oxodiperoxomolybdenum: Trialkyl(aryl)phosphine oxide complexes . Synthesis 2007 , 92 – 96 .
   Google Scholar
• Hamamoto , M. ; Nakayama , K. ; Nishiyama , Y. ; Ishii , Y. Oxidation of organic substrates by a molecular oxygen/aldehyde/heteropolyoxometalate system . J. Org. Chem. 1993 , 58 , 6421 – 6425 .
   Web of Science ®Google Scholar
• SciFinder Scholar: 13C NMR, Spectrum ID CNCC-74760-160M. Spectral data were obtained from Wiley Subscripton Services, Inc. (US).
   Google Scholar
• Smith , D. J. ; Patel , S. R. Acrylate and methacrylate monomers and hydrogel polymers . Eur. Pat. Appl. 0263605 , September 15 , 1987 .
   Google Scholar
• Bolton , G. L. ; Padia , J. K. ; Trivedi , B. K. Phosphorus containing compounds as antihypercholesterolemic and antiatherosclerotic agents . U.S. Patent 5,208,224 , May 4 , 1993 .
   Google Scholar