77453-77-1Relevant academic research and scientific papers
Stereoselective synthesis of C-glycosides via Tebbe methylenation and Claisen rearrangement
Godage,Fairbanks
, p. 7589 - 7593 (2000)
A variety of β-C-glycosides may be readily accessed in a stereoselective fashion from 3-OH glycal esters, via the use of Tebbe methylenation and subsequent thermal Claisen rearrangement. The use of carbohydrate ester substrates allows the formation of β(1
Stereoselective synthesis of C-glycosides from carboxylic acids: The tandem Tebbe-Claisen approach
Godage, H. Yasmin,Chambers, David J.,Evans, Graham R.,Fairbanks, Antony J.
, p. 3772 - 3786 (2007/10/03)
A variety of β- or α-C-glycosides may be readily accessed in an entirely stereoselective fashion from esters derived from the reaction of carboxylic acids and 3-hydroxy glycals, by way of a tandem reaction sequence of Tebbe methylenation and Claisen rearrangement. Though of wide scope, for example allowing the synthesis of 1-6 linked C-disaccharides, the methodology does not currently allow the synthesis of C-glycosyl α-amino acids.
Reaction of 4,6-O-Benzylideneglycals with Benzoic Acid, Triphenylphosphine, and Diethyl Azodicarboxylate and of the Products with Sodium Methoxyde. X-Ray Structure of 1-O-Benzoyl-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranose, C21H22O6
Guthrie, R. D.,Irvine, Robert W.,Davison, Bruce E.,Henrick, Kim,Trotter, Jill
, p. 468 - 472 (2007/10/02)
Reaction of 4,6-O-benzylidene-D-allal with benzoic acid, triphenylphosphine, and diethyl azodicarboxylate gave a mixture of 1-O-benzoyl-4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranose (3) as the major product together with its β-anomer (4) and 3-O-benzoyl-4,6-O-benzylidene-D-glucal (5).Debenzoylation led to a mixture of the 4,6-O-benzylidene-D-glucal, 4,6-O-benzylidene-2-deoxy-3-O-methyl-D-arabino- and -D-ribo-hexopyranose.The structure of the arabino-isomer (6) was established by X-ray analysis of its 1-O-benzoyl derivative.Crystals are orthorhombic, space group P212121, a=21.789(2), b=14.772(3), c=5.925(2) Angstroem.The structure was solved by direct methods and refined to R 0.095.
Allylic Nucleophilic Substitution Reactions in Sugars. III. Uncatalysed Displacements in Hexamethylphosphoramide
Guthrie, R. D. (Gus),Irvine, Robert W.,Jenkins, Ian D.
, p. 2499 - 2508 (2007/10/02)
The uncatalysed displacement of allylic benzoyloxy groups with azide in unsaturated sugars has been studied by using hexamethylphosphoramide as solvent.Tri-O-benzoylglycals and 4,6-O-benzylidene-3-O-benzoylglycals were investigated.The former gave rise to
