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Volumn 61, Issue 14, 1996, Pages 4582-4588

Enantioselective synthesis of L- and D-carboranylalanine

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE DERIVATIVE; CARBORANE DERIVATIVE; CARBORANYLALANINE; ORGANOBORON DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0029931097     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952271b     Document Type: Article
Times cited : (59)

References (35)
  • 1
    • 15844398242 scopus 로고    scopus 로고
    • note
    • 2O).
  • 2
    • 0028297726 scopus 로고
    • Hatanaka, H.; Nakagawa, Y. Int. Rad. Oncol. 1994, 28, 1061-1066. Hawthorne, M. F. Angew. Chem., Int. Ed. Engl. 1993, 32, 950-984. Slatkin, D. N. Brain 1991, 114, 1609-1629. Fairchild, R. G.; Wheeler, F.; Slatkin, D. N.; Coderre, J.; Micca. P.; Laster, B.; Kahl, S. B.; Som, P.; Fand, I. Strahlenther. Onkol. 1989, 165, 343-347.
    • (1994) Int. Rad. Oncol. , vol.28 , pp. 1061-1066
    • Hatanaka, H.1    Nakagawa, Y.2
  • 3
    • 33745945620 scopus 로고
    • Hatanaka, H.; Nakagawa, Y. Int. Rad. Oncol. 1994, 28, 1061-1066. Hawthorne, M. F. Angew. Chem., Int. Ed. Engl. 1993, 32, 950-984. Slatkin, D. N. Brain 1991, 114, 1609-1629. Fairchild, R. G.; Wheeler, F.; Slatkin, D. N.; Coderre, J.; Micca. P.; Laster, B.; Kahl, S. B.; Som, P.; Fand, I. Strahlenther. Onkol. 1989, 165, 343-347.
    • (1993) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 950-984
    • Hawthorne, M.F.1
  • 4
    • 0025895856 scopus 로고
    • Hatanaka, H.; Nakagawa, Y. Int. Rad. Oncol. 1994, 28, 1061-1066. Hawthorne, M. F. Angew. Chem., Int. Ed. Engl. 1993, 32, 950-984. Slatkin, D. N. Brain 1991, 114, 1609-1629. Fairchild, R. G.; Wheeler, F.; Slatkin, D. N.; Coderre, J.; Micca. P.; Laster, B.; Kahl, S. B.; Som, P.; Fand, I. Strahlenther. Onkol. 1989, 165, 343-347.
    • (1991) Brain , vol.114 , pp. 1609-1629
    • Slatkin, D.N.1
  • 13
    • 15844368029 scopus 로고    scopus 로고
    • note
    • For many applications, the difference between incorporating a meta-carborane cage into the amino acid or incorporating an o-carborane functionality was not important.
  • 18
    • 0008902080 scopus 로고
    • Kabalka, G. W., Ed.; Royal Society of Chemistry: Cambridge, U.K.
    • Kahl, S. B.; Radel, P. A. Current Topics In The Chemistry of Boron; Kabalka, G. W., Ed.; Royal Society of Chemistry: Cambridge, U.K. 1994; pp 155-160.
    • (1994) Current Topics in the Chemistry of Boron , pp. 155-160
    • Kahl, S.B.1    Radel, P.A.2
  • 20
    • 0342754732 scopus 로고
    • A one-pot sequence to obtain the carboxylic acid directly from allylcarborane by oxidation of the intermediate organoborane according to the method of Perisamy (Perisamy, M.; Narayana, C.; Anitha, N. Indian J. Chem. 1986, 25B, 844-846) was not successful.
    • (1986) Indian J. Chem. , vol.25 B , pp. 844-846
    • Perisamy, M.1    Narayana, C.2    Anitha, N.3
  • 23
    • 15844430582 scopus 로고    scopus 로고
    • note
    • 2O, giving final solvent proportions of 1:2 (Et2O:benzene), to achieve a sufficiently polar mixture to permit reaction. The crude sublimed silyl-protected o-carborane was chromatographed on silica with hexane instead of final purification by distillation. Use of material purified in this manner, in the subsequent modified alkylation with allyl bromide, permitted 91% of the product 1-silyl 2-allyl o-carborane to be isolated, after chromatographic purification on silica gel.
  • 27
    • 15844385262 scopus 로고    scopus 로고
    • note
    • This improved overall yield differs from that in Scheme 4; it is the result of carrying crude bromo imide on to the azido imide intermediate. Scheme 4 reports stepwise yields, after chromatography. The bromo imide is susceptible to decomposition on silica gel.
  • 29
    • 0003998388 scopus 로고    scopus 로고
    • CRC Press: Cleveland, OH
    • The rotation had been reported using water as the solvent. Attempts to dissolve the stated amount of amino acid were not successful. Phenylalanine itself, a less hydrophobic amino acid, is only soluble to the extent of 2.96 g/100 mL of water. (Handbook of Chemistry and Physics, 55th Ed.; Weast, R. C., Ed.; CRC Press: Cleveland, OH, 1974; C-743). Attempts to improve the solubility by adding hydrochloric acid caused a change of sign of the rotation. This is also not unheard of for hydrophobic amino acids. Leucine is an example (Ibid., p C-742).
    • (1974) Handbook of Chemistry and Physics, 55th Ed.
    • Weast, R.C.1
  • 30
    • 0003998388 scopus 로고    scopus 로고
    • The rotation had been reported using water as the solvent. Attempts to dissolve the stated amount of amino acid were not successful. Phenylalanine itself, a less hydrophobic amino acid, is only soluble to the extent of 2.96 g/100 mL of water. (Handbook of Chemistry and Physics, 55th Ed.; Weast, R. C., Ed.; CRC Press: Cleveland, OH, 1974; C-743). Attempts to improve the solubility by adding hydrochloric acid caused a change of sign of the rotation. This is also not unheard of for hydrophobic amino acids. Leucine is an example (Ibid., p C-742).
    • Handbook of Chemistry and Physics, 55th Ed.
  • 33
    • 15844393073 scopus 로고    scopus 로고
    • note
    • Several other columns and conditions were evaluated for their utility; neither Nucleosil-2 nor Chiralcel OT columns permitted separation of the isomers.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.