By Helen M.I. Osborn (Eds.)

Content material:

, Page vii
Contributors to this Volume

, Pages ix-x

, Pages xix-xxii
1 - An advent to Carbohydrate Synthesis

, Pages 1-8, Helen Osborn
2 - Selective Hydroxyl defense and Deprotection

, Pages 9-68, Jeremy Robertson, Petra M. Stafford
3 - Synthesis and Activation of Carbohydrate Donors: Acetates, Halides, Phenyl selenides and Glycals

, Pages 69-120, Benjamin G. Davis, David Chambers, Ian Cumpstey, Robert France, David Gamblin
4 - Synthesis and Activation of Carbohydrate Donors: Thioglycosides and Sulfoxides

, Pages 121-145, K.P. Ravindranathan Kartha, Robert A. Field
5 - Synthesis and Activation of Carbohydrate Donors: Acetimidates, n-Pentenyl and Vinyl Glycosides

, Pages 147-194, Antony J. Fairbanks, Christopher M.P. Seward
6 - glossy Glycosidation equipment: Tuning of Reactivity

, Pages 195-218, Jörg Pietruszka
7 - sleek Glycosidation equipment: Orthogonal Glycosidation

, Pages 219-238, Jörg Pietruszka
8 - The Stereoselective Synthesis of β-Mannosides

, Pages 239-276, Seth C. Ennis, Helen M.I. Osborn
9 - Synthesis of Sialic Acid Containing Carbohydrates

, Pages 277-310, Hiromune Ando, Hideharu Ishida, Makoto Kiso
10 - The Synthesis of Glycosyl Amino Acids

, Pages 311-336, Philip G. Evans, Natasha Gemmell, Osborn Helen M.I.
11 - The Synthesis of C-Linked Glycosides

, Pages 337-384, Paul Meo, Helen M.I. Osborn
12 - The makes use of of Glycoprocessing Enzymes in Synthesis

, Pages 385-426, Benjamin G. Davis, Susan M. Hancock

, Pages 427-430

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Sample text

Method 13 [99] Preparation of methyl-4,6-O-(1,1,3,3-tetra-isopropyldisiloxanylidene)-1-thio-a-D mannopyranoside. 7 EXPERIMENTAL PROCEDURES 53 TIPDSCl2, imidazole, 0 8C, 30 min. Notes. Kinetic double silylation of the 4,6-diol under mildly basic conditions initiated by reaction at the sterically most available 6-OH. Materials. 8 mmol) harmful, corrosive Acetonitrile (anhydrous, 60 ml) highly flammable, toxic Methanol (10 ml) highly flammable, toxic Celitew harmful by inhalation, possible irreversible effects Toluene (few ml) highly flammable, harmful, irritant Ethyl acetate (chromatography solvent) highly flammable, irritant Hexane (chromatography solvent) highly flammable, harmful Equipment.

In the context of carbohydrate protection, two acetal derivatives dominate: benzylidene and isopropylidene (acetonide). The two are complementary both in terms of their site selectivity and of their deprotection chemistry, and the choice of which to use, therefore, is normally quite clear. Under ‘classical’ conditions (acid-catalysed [74] condensation of the sugar with either acetone or benzaldehyde with removal of water) the reactions are subject to thermodynamic control and the major products can be rationalised on stability grounds.

50 mmol) harmful, irritant, toxic Distilled water (3 ml) no risk Ammonia solution (50% aqueous, 3 ml) corrosive, irritant Ethyl acetate (5 £ 5 ml) highly flammable, irritant Magnesium sulfate (drying agent) irritant, harmful by inhalation Dichloromethane (chromatography solvent) toxic, irritant, possible irreversible effects Acetone (chromatography solvent) highly flammable Triethylamine highly flammable, corrosive, harmful Equipment. Drying pistol Two-necked round bottomed flask (25 ml) with rubber septum and magnetic stirrer bar Reflux condenser Source of inert gas Heater stirrer with thermostat thermometer Oil bath Syringes (10 ml and 200 ml) Column chromatography equipment Procedure.

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