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10
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34548284069
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C. Rademacher G. K. Shoemaker H. S. Kim R. B. Zheng H. Taha C. Liu R. C. Nacario D. C. Schriemer J. S. Klassen T. Peters T. L. Lowary J. Am. Chem. Soc. 2007 129 10489
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(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 10489
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Rademacher, C.1
Shoemaker, G.K.2
Kim, H.S.3
Zheng, R.B.4
Taha, H.5
Liu, C.6
Nacario, R.C.7
Schriemer, D.C.8
Klassen, J.S.9
Peters, T.10
Lowary, T.L.11
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17
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47949106177
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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
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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
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21
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0343812106
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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:
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A. F. Bochkov Y. V. Voznyi V. N. Chernetskii V. M. Dashunin A. V. Rodionov Izv. Akad. Nauk. SSSR, Ser. Khim. 1975 420
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(1975)
Izv. Akad. Nauk. SSSR, Ser. Khim.
, pp. 420
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Bochkov, A.F.1
Voznyi, Y.V.2
Chernetskii, V.N.3
Dashunin, V.M.4
Rodionov, A.V.5
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23
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0034696872
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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
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T. Bamhaoud S. Sanchez J. Prandi Chem. Commun. 2000 659
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(2000)
Chem. Commun.
, pp. 659
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Bamhaoud, T.1
Sanchez, S.2
Prandi, J.3
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25
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0033890915
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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:
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M. Hori F. Nakatsubo Macromolecules 2000 33 1148
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(2000)
Macromolecules
, vol.33
, pp. 1148
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Hori, M.1
Nakatsubo, F.2
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