74774-10-0Relevant articles and documents
Stereospecific synthesis of methyl 2-amino-2-deoxy-(6S)-deuterio-α,β-D-glucopyranoside and methyl 2,6-diamino-2,6-dideoxy-(6R)-deuterio-α,β-D-glucopyranoside: Side chain conformations of the 2-amino-2-deoxy and 2,6-diamino-2,6-dideoxyglucopyranosides
Kato, Takayuki,Vasella, Andrea,Crich, David
, p. 10 - 17 (2017)
The stereospecifically labeled 6-monodeuterio methyl 2,6-diamino-2,6-dideoxy-α- and β- D-glucopyranosides were synthesized with a view to determining their side chain conformations. NMR studies in D2O at pH 5 and pH 11 reveal both anomers to adopt very predominantly the gt conformation consistent with the gauche conformation of 2-aminoethanol and its acetate salt. In contrast, as also revealed with the help of stereospecifically-labelled monodeuterio isotopomers, the methyl 2-amino-2-deoxy-α- and β- D-glucopyranosides are an approximately 1:1 mixture of gg and gt conformers as is found in glucopyranose itself.
Photobromination of Carbohydrate Derivatives. VI. Funcionalization at C6 of 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-glucopyranose
Ferrier, Robert J.,Furneaux, Richard H.
, p. 1025 - 1036 (2007/10/02)
Photobromination of 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-glucopyranose gives the syrupy 6S (exo) bromide in high yield; further reaction leads to secondary bromination at this position.The monobromide reacts with methanol and thiophenol under conditions of kinetic control to give mainly the endo-methoxy and phenylthio derivatives formed by direct nucleophilic displacement, and from the latter the exo-methoxy acetal was obtained by a second nucleophilic substitution.Acetolysis of these compounds can lead to the coresponding exo-6-acetoxy ester or monocyclicproducts formed by opening of the five-membered rings.
