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Volumn 3, Issue 3, 1997, Pages 431-440

A new strategy for oligosaccharide assembly exploiting cyclohexane-1,2-diacetal methodology: An efficient synthesis of a high mannose type nonasaccharide

Author keywords

carbohydrates; glycoproteins; HIV; oligosaccharides; protecting groups

Indexed keywords


EID: 0030892662     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030315     Document Type: Article
Times cited : (110)

References (71)
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    • For the synthesis of major segments of high mannose glycoproteins see: H. Paulsen, Angew. Chem. 1990, 102, 851; Angew. Chem. Int. Ed. Engl. 1990, 29, 823, and references therein. A synthesis of the protected nonamannan has been reported recently: J. R. Merritt, E. Naisang, B. Fraser-Reid. J. Org. Chem. 1994, 59, 4443.
    • (1990) Angew. Chem. , vol.102 , pp. 851
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    • and references therein
    • For the synthesis of major segments of high mannose glycoproteins see: H. Paulsen, Angew. Chem. 1990, 102, 851; Angew. Chem. Int. Ed. Engl. 1990, 29, 823, and references therein. A synthesis of the protected nonamannan has been reported recently: J. R. Merritt, E. Naisang, B. Fraser-Reid. J. Org. Chem. 1994, 59, 4443.
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 823
  • 38
    • 0028086047 scopus 로고
    • For the synthesis of major segments of high mannose glycoproteins see: H. Paulsen, Angew. Chem. 1990, 102, 851; Angew. Chem. Int. Ed. Engl. 1990, 29, 823, and references therein. A synthesis of the protected nonamannan has been reported recently: J. R. Merritt, E. Naisang, B. Fraser-Reid. J. Org. Chem. 1994, 59, 4443.
    • (1994) J. Org. Chem. , vol.59 , pp. 4443
    • Merritt, J.R.1    Naisang, E.2    Fraser-Reid, B.3
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    • a) S. V. Ley, H. W. M. Priepke, S. L. Warriner, Angew. Chem. 1994, 106, 2410; Angew. Chem. Int. Ed. Engl. 1994, 33, 2290;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2290
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    • b) S. V. Ley, H. W. M. Priepke, Angew. Chem. 1994, 106, 2412; Angew. Chem. Int. Ed. Engl. 1994, 33, 2292;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 2292
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    • Recently other one-pot syntheses of trisaccharides were published: a) H. Yamada, T. Harada, T. Takahashi, J. Am. Chem. Soc. 1994, 116, 7919; b) H. K. Chenault, A. Castro, Tetrahedron Lett. 1994, 35, 9145; c) H. Yamada, T. Harada, H. Miyazaki, T. Takahashi, ibid. 1994, 35, 3979; S. Raghavan, D. Kahne, J. Am. Chem. Soc. 1993, 115, 1580; see also ref. [12b,c].
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    • Yamada, H.1    Harada, T.2    Takahashi, T.3
  • 47
    • 0028088784 scopus 로고
    • Recently other one-pot syntheses of trisaccharides were published: a) H. Yamada, T. Harada, T. Takahashi, J. Am. Chem. Soc. 1994, 116, 7919; b) H. K. Chenault, A. Castro, Tetrahedron Lett. 1994, 35, 9145; c) H. Yamada, T. Harada, H. Miyazaki, T. Takahashi, ibid. 1994, 35, 3979; S. Raghavan, D. Kahne, J. Am. Chem. Soc. 1993, 115, 1580; see also ref. [12b,c].
    • (1994) Tetrahedron Lett. , vol.35 , pp. 9145
    • Chenault, H.K.1    Castro, A.2
  • 48
    • 0028243331 scopus 로고
    • Recently other one-pot syntheses of trisaccharides were published: a) H. Yamada, T. Harada, T. Takahashi, J. Am. Chem. Soc. 1994, 116, 7919; b) H. K. Chenault, A. Castro, Tetrahedron Lett. 1994, 35, 9145; c) H. Yamada, T. Harada, H. Miyazaki, T. Takahashi, ibid. 1994, 35, 3979; S. Raghavan, D. Kahne, J. Am. Chem. Soc. 1993, 115, 1580; see also ref. [12b,c].
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3979
    • Yamada, H.1    Harada, T.2    Miyazaki, H.3    Takahashi, T.4
  • 49
    • 0027538622 scopus 로고
    • see also ref. [12b,c]
    • Recently other one-pot syntheses of trisaccharides were published: a) H. Yamada, T. Harada, T. Takahashi, J. Am. Chem. Soc. 1994, 116, 7919; b) H. K. Chenault, A. Castro, Tetrahedron Lett. 1994, 35, 9145; c) H. Yamada, T. Harada, H. Miyazaki, T. Takahashi, ibid. 1994, 35, 3979; d) S. Raghavan, D. Kahne, J. Am. Chem. Soc. 1993, 115, 1580; see also ref. [12b,c].
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 1580
    • Raghavan, S.1    Kahne, D.2
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    • for other examples see ref. [15 b,e]
    • b) H. Paulsen, Angew. Chem. 1982, 94, 184; for other examples see ref. [15 b,e].
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    • Paulsen, H.1
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    • 0343809012 scopus 로고    scopus 로고
    • note
    • Total purification of this high-polarity material was not possible at this stage.
  • 70
    • 0342503783 scopus 로고    scopus 로고
    • MCI Gel CHP 20 P (75-150 μ) from the Mitsubishi Kasei corporation, Tokyo, Japan
    • MCI Gel CHP 20 P (75-150 μ) from the Mitsubishi Kasei corporation, Tokyo, Japan.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.