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Volumn 37, Issue 51, 1996, Pages 9215-9218

First stepwise synthesis of cellulose analogs

Author keywords

[No Author keywords available]

Indexed keywords

CELLULOSE DERIVATIVE;

EID: 0030590993     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02186-7     Document Type: Article
Times cited : (16)

References (31)
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    • 2) S. Raymond, A. Heyraud, D. Tran Qui, A. Kvick, H. Chanzy, Macromolecules, 28, 2096-2100 (1995), K. Okuyama and K. Noguchi, Kobunshi, 43, 848-858 (1994), B. Henrissat, S. Perez, I. Tvaroska, W. T. Winter in "The Structure of Cellulose", American Chemical Society, 1987, pp.38-67
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    • Raymond, S.1    Heyraud, A.2    Tran Qui, D.3    Kvick, A.4    Chanzy, H.5
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    • American Chemical Society
    • 2) S. Raymond, A. Heyraud, D. Tran Qui, A. Kvick, H. Chanzy, Macromolecules, 28, 2096-2100 (1995), K. Okuyama and K. Noguchi, Kobunshi, 43, 848-858 (1994), B. Henrissat, S. Perez, I. Tvaroska, W. T. Winter in "The Structure of Cellulose", American Chemical Society, 1987, pp.38-67
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    • 3) Stepwise synthesis of cellotetraose was reported by two groups, R. R. Schmidt, J. Michel, Angew. Chem. Int. Ed. Engl., 21, 72-73 (1982), K. Takeo, K. Okushio, K. Fukuyama, T. Kuge, Carbohydr. Res., 121, 163-173 (1983).
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    • 3) Stepwise synthesis of cellotetraose was reported by two groups, R. R. Schmidt, J. Michel, Angew. Chem. Int. Ed. Engl., 21, 72-73 (1982), K. Takeo, K. Okushio, K. Fukuyama, T. Kuge, Carbohydr. Res., 121, 163-173 (1983).
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    • 5) The benzyl group at the 3-O position of the glycosyl acceptor is essential for β-glycosylation. P. Sinaÿ, Pure & Appl. Chem., 50, 1437-1452 (1978), T. Takano, F. Nakatsubo, K. Murakami, Cellulose Chem. Technol., 22, 135-145 (1988), T. Takano, Y. Harada., F. Nakatsubo, K. Murakami, Mokuzai Gakkaishi, 36, 212-217 (1990).
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    • 5) The benzyl group at the 3-O position of the glycosyl acceptor is essential for β-glycosylation. P. Sinaÿ, Pure & Appl. Chem., 50, 1437-1452 (1978), T. Takano, F. Nakatsubo, K. Murakami, Cellulose Chem. Technol., 22, 135-145 (1988), T. Takano, Y. Harada., F. Nakatsubo, K. Murakami, Mokuzai Gakkaishi, 36, 212-217 (1990).
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    • 5) The benzyl group at the 3-O position of the glycosyl acceptor is essential for β-glycosylation. P. Sinaÿ, Pure & Appl. Chem., 50, 1437-1452 (1978), T. Takano, F. Nakatsubo, K. Murakami, Cellulose Chem. Technol., 22, 135-145 (1988), T. Takano, Y. Harada., F. Nakatsubo, K. Murakami, Mokuzai Gakkaishi, 36, 212-217 (1990).
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    • 6) Generally, an electron-donating alkyl substituent increases the reactivity of the glycosyl donor in glycosylation but decreases the stability and vice versa for an acyl group. H. Paulsen, Angew. Chem. Int. Ed. Engl., 21, 155-173 (1982), T. Takano, Y. Harada, F. Nakatsubo, K. Murakami, Cellulose Chem. Technol., 24, 333-341 (1990).
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    • 6) Generally, an electron-donating alkyl substituent increases the reactivity of the glycosyl donor in glycosylation but decreases the stability and vice versa for an acyl group. H. Paulsen, Angew. Chem. Int. Ed. Engl., 21, 155-173 (1982), T. Takano, Y. Harada, F. Nakatsubo, K. Murakami, Cellulose Chem. Technol., 24, 333-341 (1990).
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    • 7) The pivaloyl group at O-2 is very useful for the highly stereoselective glycosylation, H. Kunz, A. Harreus: Liebigs. Ann. Chem., 41-48(1982).
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    • note
    • 2O was added through a rubber septum by a syringe from outside. Then, water contamination in the reaction system giving rise to the imidate hydrolysis is reduced to the minimum.(See. Ref.10)
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    • note
    • 3).
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    • Succeeded in total synthesis of poly-N-acetyl-lactosamine-type pentacosasaccharide with DP=25
    • Y. Matsuzaki, Y. Ito, Y. Nakahara, T. Ogawa
    • 19) Recently, T. Ogawa et al. succeeded in total synthesis of poly-N-acetyl-lactosamine-type pentacosasaccharide with DP=25, Y. Matsuzaki, Y. Ito, Y. Nakahara, T. Ogawa, Tetrahedron Lett., 34, 1061-1064 (1993).
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    • Ogawa, T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.