By Pavol Kováč
Long past are the times while man made courses incorporated parallel preparative experiments to rfile reproducibility of the experimental protocols and whilst journals required such documentation. the hot confirmed artificial tools sequence addresses matters to chemists relating to irreproducibility of man-made protocols, loss of characterization information for brand spanking new compounds, and inflated yields said in lots of chemical communications--trends that experience lately develop into a major challenge. quantity one among Carbohydrate Chemistry: confirmed artificial tools comprises extra special models of protocols previous Read more...
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Additional info for Carbohydrate Chemistry : Proven Synthetic Methods
Adv. Carbohydr. Chem. Biochem. 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.
1, entries 1 and 2). 7 The acetolysis protocol presented in this chapter can be extended to disaccharide and oligosaccharide derivatives. When the aglycone-bearing monosaccharide (unit A) was protected with arming protecting groups and the other one (unit B) carried disarming groups, the acetolysis proceeded selectively at the armed anomeric position to give the 1-O-Ac disaccharide (entry 3). When units A and B were both disarmed, no reaction was observed (entry 4), whereas an armed–armed disaccharide gave simultaneous cleavage of both glycosidic linkages as expected (entry 5).
The resulting solution was diluted with CH 2Cl2 (5 mL), washed with water (5 mL), and the aqueous phase was extracted with CH2Cl2 (3 × 5 mL). 9 (C-6). Anal. 57. 53. 45 mmol, 5 equiv) in dry DMF (10 mL). 5 equiv) was added at −30°C. 07). 07. 7 (OCH3). Anal. 77. 74. 5 mL). 5 equiv) as above Hex-2- and Hex-3-Enopyranosides Preparation 19 described for the preparation of 13. 74). 74. The mixture was cooled to −30°C and the excess of NaH was destroyed by addition of MeOH (2 mL). After 10 min, the solution was poured into a mixture of ice and ether, the two layers were separated and the aqueous phase was further extracted with ether (2 × 15 mL).