74774-22-4Relevant academic research and scientific papers
Synthesis of unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose via stereoselective photobromination of 2,3-isopropylidene-4-benzoyl-1,6-anhydro-β-D-mannopyranose
Mahdi, Jassem G.,Dawoud, Hanaa M.,Manning, Abigail J.,Lieberman, Harvey F.,Kelly, David R.
, p. 24 - 35 (2019/11/03)
Stereoselective photobromination of 1,6-anhydro-β-D-glucopyranose derivatives occurs at exo-H6. However, photobromination of 4-benzoyl-2,3-isopropylidene-1,6-anhydro-β-D-mannopyranose 6 produced unstable 4-benzoyl-1,6-anhydro-3-keto-β-D-mannopyranose 7. The mechanism of stereoselective oxidation at C-3 could be attributed to the facile radical proton abstraction at C-3, followed by the subsequent bromination of the isopropylidene group, which was subsequently eliminated during the aqueous workup. Thus, the aim of this article is to identify the molecular structure of the unstable compound 7.
Free radical alkylation of tri-o-benzoyl-6-exo-bromo-levoglucosan: Approaches to the synthesis of okadaic acid
Kelly, David R,Mahdi, Jassem G
, p. 511 - 514 (2007/10/03)
Tri-O-benzoyl-6-exo-bromo-levoglucosan undergoes stereoselective free radical alkylation to give 6-exo-substituted-1,6-anhydrosugars with six contiguous chiral centres.
Synthesis of (6R)- and (6S)-D-Glucose-6-(2)H through Stereospecific Photo-bromination of 1,6-Anhydro-β-D-glucopyranose Derivative
Ohrui, Hiroshi,Horiki, Hiroyuki,Kishi, Hisahi,Meguro, Hiroshi
, p. 1101 - 1106 (2007/10/02)
A photo-bromination of 1,6-anhydro-2,3,4-tri-O-benzoyl-β-D-glucopyranose and its -derivative gave the corresponding (6S)-6-bromo compounds stereospecifically.They were transformed into (6S)-D-glucose-6-(2)H and (6R)-D-glucose-6-(2)H respectivel
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.
