Carbohydrate Chemistry : Proven Synthetic Methods by Pavol Kováč
By Pavol Kováč
Gone are the times while artificial guides incorporated parallel preparative experiments to record reproducibility of the experimental protocols and whilst journals required such documentation. the hot confirmed man made tools sequence addresses issues to chemists relating to irreproducibility of artificial protocols, loss of characterization information for brand spanking new compounds, and inflated yields pronounced in lots of chemical communications--trends that experience lately develop into a major challenge. quantity certainly one of Carbohydrate Chemistry: confirmed artificial equipment contains extra designated models of protocols previous Read more...
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2003, 58, 55–119. 2. Hanessian, S. , 1983. 3. Danishefsky, S. ; Bilodeau, M. T. Angew. Chem. Int. Ed. Engl. 1996, 35, 1380–1419. 4. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57–66. 5. (a) Chètrien, F. Synth. Commun. 1989, 19, 1015–1024; (b) Khan, K. ; Shah, S. T. ; Shekhani, M. ; Volter, W. New. J. Chem. ; Vittorino, E. Carbohydr. Res. 2003, 338, 2349–2358. 6. (a) Binkley, R. ; Ambrose, M. G. J. Carbohydr. Chem. ; Kobayashi, Y. Carbohydr. Res. ; Tsuchiya, T. Carbohydr. Res. ; Tsuchiya, T. Carbohydr.
Mel, Ag/O, Me2S B. Mel, Ag/O OH BnO HO 2 CH2OTr O MeO OMe A. Mel, Ag/O, Me2S B. Mel, Ag/O OH MeO CH2OTr O OMe OMe 3 HO HO OMe OMe 1 HO CH2OMe O 4 CH2OTr O HO 5 A. Mel, Ag/O, Me2S OMe B. Mel, Ag/O MeO MeO CH2OTr O MeO OMe 6 * Corresponding author. † Checker. 27 28 Carbohydrate Chemistry: Proven Synthetic Methods HO BnO CH2OBz O OBn 7 OMe A. Mel, Ag/O, Me2S B. 2 This method is, however, still useful when more powerful reagents cannot be applied because of synthon instability. Although its exact role has not been established, the addition of a catalytic amount of dimethyl sulfide to Purdie reagent has been shown3,4 to affect the rate of O-methylation markedly and to yield permethylated product in cases where the standard Purdie procedure resulted in only partial methylation.
9 MHz (13C) in the reported solvent (internal standard Me4Si) and the assignments were made, when possible, with DEPT, HETCOR, and COSY experiments. All reactions were followed by TLC on Kieselgel 60 F254 with detection by UV light and/or by charring with 10% sulfuric acid in ethanol. Kieselgel 60 (Merck, 230–400 mesh) was used for flash chromatography. Solvents were dried by distillation according to standard procedures,11 and were stored over activated molecular sieves. Solutions in organic solvents were dried with MgSO4.