By Helen M.I. Osborn (Eds.)
, 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 security 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 - sleek Glycosidation tools: 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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Cool the solution to room temperature and remove the solvents in vacuo to afford the crude product as a yellow solid. 40 g, 80%). 48 (m, ArH, 10H); MS m/z (ESI), 373 (M þ Na). Method 6  Preparation of di-1,6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(2-O-acetyl-3-Obenzyl-4-O-para-methoxybenzyl-6-O-tert-butyl-dimethylsilyl-a-L -idopyranosyl)D -glucopyranose. PMBO – C(vNH)CCl3, cat. TfOH, rt, 2 h. Notes. Alkylation under mildly acidic conditions. Protonation of the alkyl trichloroacetimidate (at nitrogen) activates the electrophile towards nucleophilic attack by the hydroxyl group of the sugar to generate the alkyl ether and liberate trichloroacetamide.
E. the 4,6-O-isopropylidene derivative, that derives from initial reaction at the (least hindered) 6-OH. 59). 60) . Once in place, both isopropylidene and benzylidene functionality survive many routine synthetic operations and, when no longer required, may be readily removed by hydrolysis. Two aspects of acetal deprotection are of interest here: (1) partial hydrolysis of bis-acetals, particularly bis(isopropylidenes); and (2) protecting group interchange, particularly of benzylidenes. 60 32 2.
Notes. Palladium on carbon and palladium(II) acetate are also commonly used to effect deprotection. Materials. 00 mmol) assume toxic Methanol (20 þ 3 £ 5 ml þ chromatography solvent) highly ﬂammable, toxic Hydrogen highly ﬂammable, forms explosive mixtures with air Celitew Dichloromethane (chromatography solvent) Equipment. Round bottomed ﬂask (100 ml) with magnetic stirrer bar Quickﬁt three-way tap harmful by inhalation, possible irreversible effects toxic, irritant, possible irreversible effects 48 2.