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Volumn 61, Issue 20, 1996, Pages 6873-6880

Total synthesis of sialylgalactosylgloboside: Stage-specific embryonic antigen 4

Author keywords

[No Author keywords available]

Indexed keywords

ANTIGEN; GLYCOSPHINGOLIPID; SIALYLGALACTOSYLGLOBOSIDE; STAGE SPECIFIC EMBRYO ANTIGEN 4; UNCLASSIFIED DRUG;

EID: 0029802668     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9608073     Document Type: Article
Times cited : (42)

References (50)
  • 32
    • 0000013034 scopus 로고
    • This compound was first synthesized by Ogawa's group: Sato, S.; Nunomura, S.; Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 4097. The low overall yield and length (14 steps) of the synthesis, however, prompted us to develop a shorter, more efficient synthesis of this compound: Lassaletta, J. M.; Schmidt, R. R. Synlett 1995, 925.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4097
    • Sato, S.1    Nunomura, S.2    Nakano, T.3    Ito, Y.4    Ogawa, T.5
  • 33
    • 79955657835 scopus 로고
    • This compound was first synthesized by Ogawa's group: Sato, S.; Nunomura, S.; Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 4097. The low overall yield and length (14 steps) of the synthesis, however, prompted us to develop a shorter, more efficient synthesis of this compound: Lassaletta, J. M.; Schmidt, R. R. Synlett 1995, 925.
    • (1995) Synlett , pp. 925
    • Lassaletta, J.M.1    Schmidt, R.R.2
  • 35
    • 16044371644 scopus 로고
    • Diplomarbeit, University of Konstanz
    • (b) Rademann, J. Diplomarbeit, University of Konstanz, 1994.
    • (1994)
    • Rademann, J.1
  • 36
    • 16044373072 scopus 로고    scopus 로고
    • note
    • This compound was obtained in good yield by direct anomeric O-alkylation of 4,6-O-benzylidenegalactopyranose (see Experimental Section).
  • 41
    • 16044370511 scopus 로고    scopus 로고
    • note
    • Though the phosphite methodology (see ref 19) usually yields virtually complete α-selectivities, other rather unpredictable results have been observed for related systems. This result, however, can be considered as acceptable due to the high yield obtained.
  • 44
    • 0001339291 scopus 로고
    • John Wiley and Sons Inc.: New York
    • Fieser, L. F.; Fieser, M. In Reagents for Organic Synthesis; John Wiley and Sons Inc.: New York, 1967; Vol. 1, p 782. The age of the catalyst was found to be of importance; in our hands, the use of old catalysts led to complex mixtures containing the desired product in low yield.
    • (1967) Reagents for Organic Synthesis , vol.1 , pp. 782
    • Fieser, L.F.1    Fieser, M.2
  • 46
    • 16044366293 scopus 로고    scopus 로고
    • note
    • 1H NMR data reported for SGG in ref 18 are erroneous.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.