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von Gadow, A.; Joubeit, E.; Hansmann, C. F. J. Agric Food. Chem. 1997, 45, 632.
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6
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Shimamura, N.1
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9
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0030048492
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(a) Kawamoto, H.; Nakatsubo, F.; Murakami, K. Synth. Commun. 1996, 26, 531.
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10
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77950208746
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2O, Pyr).
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2O, Pyr).
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11
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77950196287
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3 (5 equiv) in. DMF at 80 °C for 1 h.
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3 (5 equiv) in. DMF at 80 °C for 1 h.
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14
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0037467849
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1H NMR analysis of the individual a and β Cl anomers of dipivaloate 4a.
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1H NMR analysis of the individual a and β Cl anomers of dipivaloate 4a.
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Rani, S.1
Vankar, Y.D.2
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15
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77950210659
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Attempts to achieve greater conversions in the C-glycosylation reactions by adding excess Lewis acid (>10 equiv), by elevating the reaction temperature (*25 °C), or by increasing the reaction time (>lh) only led to lower overall yields of 5, presumably due to acid-induced cleavage of the aromatic benzyl ether protecting groups.
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Attempts to achieve greater conversions in the C-glycosylation reactions by adding excess Lewis acid (>10 equiv), by elevating the reaction temperature (*25 °C), or by increasing the reaction time (>lh) only led to lower overall yields of 5, presumably due to acid-induced cleavage of the aromatic benzyl ether protecting groups.
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16
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0035052372
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Desmares, G.; Lefebvre, D.; Renevret, G.; Le Drian, C. Helv. Chim. Acta 2001, 84, 880.
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Desmares, G.1
Lefebvre, D.2
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Le Drian, C.4
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17
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77950262792
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Prepared in the same manner as 4a, except with the substitution of isobutryl chloride for pivaloyl chloride in the esteriflcaton step
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(a) Prepared in the same manner as 4a, except with the substitution of isobutryl chloride for pivaloyl chloride in the esteriflcaton step
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18
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77950277171
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Prepared in the same manner as 4a, except with the substitution of cyclohexyl carbonyl chloride for pivaloyl chloride in the esteriflcaton. step.
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(b) Prepared in the same manner as 4a, except with the substitution of cyclohexyl carbonyl chloride for pivaloyl chloride in the esteriflcaton. step.
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19
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0034967020
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Nay, B.; Arnaudinaud, V.; Vercauteren, J. Eur. J. Org. Chem. 2001, 12, 2379.
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24
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25
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77950241091
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Glycoside 5b could also be used in the Vilsmeier formylation reaction, providing an 83% yield of the corresponding isobutyryl-protected aryl aldehyde. This substrate was not chosen to advance through the remainder of the synthesis for two reasons; first, the cost of isobutyryl chloride required for the preparation of 4b (and thus 5b) is about twice that of pivaloyl chloride, and second, slightly lower overall yields (∼55%) were obtained when the isobutyryl-protected aryl aldehyde was subjected to the coupling (with lithiated 10a and 10b) and isobutyrate deprotection reactions.
-
Glycoside 5b could also be used in the Vilsmeier formylation reaction, providing an 83% yield of the corresponding isobutyryl-protected aryl aldehyde. This substrate was not chosen to advance through the remainder of the synthesis for two reasons; first, the cost of isobutyryl chloride required for the preparation of 4b (and thus 5b) is about twice that of pivaloyl chloride, and second, slightly lower overall yields (∼55%) were obtained when the isobutyryl-protected aryl aldehyde was subjected to the coupling (with lithiated 10a and 10b) and isobutyrate deprotection reactions.
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26
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58149127315
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4-Benzyloxybenzaldehyde
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4-Benzyloxybenzaldehyde: Narasimhulu, M.; Srikanth Reddy, T.; Chinni Mahesh, K.; Sai Krishna, A.; Venkateswara Rao, J.; Venkateswarlu, Y. Bioorg. Med. Chem. Lett. 2009, 19, 3125.
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33750209029
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3,4-Bis(benzyloxy)benzaldehyde
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Rego, A.6
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(a) Muller, S.; Liepold, B.; Roth, R. G.; Bestmann, H. J. Synlett 1996, 521.
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