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Volumn , Issue 30, 2008, Pages 3510-3512

Automated synthesis of lipomannan backbone α(1-6) oligomannoside via glycosyl phosphates: Glycosyl tricyclic orthoesters revisited

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; MANNOSIDE; PHOSPHATE;

EID: 47949091471     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b804069a     Document Type: Article
Times cited : (26)

References (28)
  • 12
  • 17
    • 47949106177 scopus 로고    scopus 로고
    • We are aware that the TIPS group is not the only protecting group that could be chosen for this purpose. However, the steric bulk and base-stable nature of TIPS make it the ideal choice in this case
    • We are aware that the TIPS group is not the only protecting group that could be chosen for this purpose. However, the steric bulk and base-stable nature of TIPS make it the ideal choice in this case
  • 21
    • 0343812106 scopus 로고
    • Prandi et al. have reported the CSA-catalyzed trans-orthoesterification of 1,2-orthoarabinose to the tricyclic 1,2,5-orthoester. These tricyclic orthoesters were reacted with thiols to give thioglycosides, which were used in the syntheses of oligoarabinofuranosides. See:
    • A. F. Bochkov Y. V. Voznyi V. N. Chernetskii V. M. Dashunin A. V. Rodionov Izv. Akad. Nauk. SSSR, Ser. Khim. 1975 420
    • (1975) Izv. Akad. Nauk. SSSR, Ser. Khim. , pp. 420
    • Bochkov, A.F.1    Voznyi, Y.V.2    Chernetskii, V.N.3    Dashunin, V.M.4    Rodionov, A.V.5
  • 23
    • 0034696872 scopus 로고    scopus 로고
    • Glycosyl phosphates are currently easier to use for automated synthesis than thioglycosides because glycosyl phosphates can be activated under homogeneous reaction conditions with a single activator, such as TMSOTf
    • T. Bamhaoud S. Sanchez J. Prandi Chem. Commun. 2000 659
    • (2000) Chem. Commun. , pp. 659
    • Bamhaoud, T.1    Sanchez, S.2    Prandi, J.3
  • 25
    • 0033890915 scopus 로고    scopus 로고
    • The acid-induced trans-orthoesterification of glycosyl 1,2-orthoesters has been described in the literature; see refs. 9, 10 and 11a. However, we were unable to reproduce the results of Bochkov et al. (see ref. 9c), reporting that para-toluenesulfonic acid can induce the trans-orthoesterification of 2g to the corresponding tricyclic orthoester in 48% yield (our result: 26%). Hiranuma et al. (ref. 11a) reported the formation of a mannosyl tricyclic orthoester using pyridine as the solvent and pyridium trifluoromethanesulfonate as the acid catalyst. However, these conditions are less practical for scale-up 1,2-Orthoesters were prepared in four steps from d-mannose, d-glucose or d-xylose in good yield. See ESI Tricyclic orthoesters have been used as protecting groups for carboxylic acids, and they require fairly vigorous conditions for cleavage. See:
    • M. Hori F. Nakatsubo Macromolecules 2000 33 1148
    • (2000) Macromolecules , vol.33 , pp. 1148
    • Hori, M.1    Nakatsubo, F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.