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Volumn , Issue 5, 2003, Pages 689-693

Diastereoselective synthesis of 3-phosphonomethyl-substituted cyclohexyl- and cyclohex-2-enylglycines

Author keywords

1,3 dienylphosphonates; Conjugate addition; Cyclohexylglycines; Phosphono amino acids; Stereoselectivity

Indexed keywords

GLYCINE; GLYCINE DERIVATIVE; LEUCINE; LITHIUM DERIVATIVE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; PHOSPHONIC ACID DERIVATIVE;

EID: 0037266873     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (3)

References (33)
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    • note
    • New address: S. Conde, Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, USA.
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    • Pharmacology of NMDA receptors
    • Egebjerg, J.; Schousboe, A.; Krogsgaard-Larsen, P., Eds.; Taylor & Francis: London, UK
    • Jane, D. Pharmacology of NMDA receptors, in Glutamate and GABA Receptors and Transporters; Egebjerg, J.; Schousboe, A.; Krogsgaard-Larsen, P., Eds.; Taylor & Francis: London, UK, 2002, 69.
    • (2002) Glutamate and GABA Receptors and Transporters , pp. 69
    • Jane, D.1
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    • 0037134146 scopus 로고    scopus 로고
    • Cyclohexylglycines are attractive molecules for the pharmaceutical industry, as they are widely found in natural products and their incorporation into peptide inhibitors renders resistance to peptidases and impart pharmaceutical stability. See: Venkatraman, S.; Njoroge, F. G.; Girijavallabhan, V.; McPhail, A. T. J. Org. Chem. 2002, 67, 2686.
    • (2002) J. Org. Chem. , vol.67 , pp. 2686
    • Venkatraman, S.1    Njoroge, F.G.2    Girijavallabhan, V.3    McPhail, A.T.4
  • 20
    • 0013162145 scopus 로고    scopus 로고
    • note
    • 2 or RP-18), and their spectral data (IR, FABMS and NMR) were consistent with the proposed structures.
  • 21
    • 0013072157 scopus 로고    scopus 로고
    • note
    • 4JC2′-P(cis) values range from 6.4-9.2 Hz.
  • 22
    • 0013074931 scopus 로고    scopus 로고
    • note
    • Multigram quantities of (2S)-2-tert-butyl-3,6-dietoxy-2,5-dihydropyrazine were obtained from Novartis Kilo Laboratory. When (2S)-2,5-dihydro-3,6-dimetoxy-2-isopropylpyrazine (available from Fluka and Merck) was used for the reaction with 3a,b and 4a,b, analogous yields and selectivities were obtained. The excess of Schöllkopf's reagent could be almost completely recovered, and showed no racemization.
  • 28
    • 0013073289 scopus 로고    scopus 로고
    • note
    • 2O) δ: 30.45.
  • 29
    • 0000383803 scopus 로고
    • For previous NBS-mediated lactonizations of 2-amino-4-pentenoic acid derivatives, see: Ohfune, Y.; Hori, K.; Sakaitani, M. Tetrahedron Lett. 1986, 27, 6079.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 6079
    • Ohfune, Y.1    Hori, K.2    Sakaitani, M.3
  • 31
    • 0013124798 scopus 로고    scopus 로고
    • note
    • 22 as implemented in the Gaussian 98 program package, revision A. 11. Density functional theory treatment was reduced to an inner model constituted by lithiated dihydropyrazinone and butadienylphosphonic acid in the presence of two water molecules. Ethyl groups were replaced by methyl ones in the complete models.
  • 33
    • 0013163176 scopus 로고    scopus 로고
    • note
    • Most stable disolvated TSs located at the ONIOM[B3LYP/6-31G (d):PM3] level of theory for the addition of 2 to (4R)-4b and (4S)-4b are shown in Figure 2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.