87791-22-8

Upstream product

• 74-83-9 methyl bromide 
• 108-24-7 acetic anhydride 
• 39686-94-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose 
• 39708-10-6 methyl 3-O-benzyl-2,4,6-tri-O-methyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Impact of Aromatic Stacking on Glycoside Reactivity: Balancing CH/πand Cation/πInteractions for the Stabilization of Glycosyl-Oxocarbenium Ions

Carbohydrate/aromatic stacking represents a recurring key motif for the molecular recognition of glycosides, either by protein binding domains, enzymes, or synthetic receptors. Interestingly, it has been proposed that aromatic residues might also assist i

Synthesis of 2-Acyloxy- and 2-Alkoxy-3-oxoglycals and of Their Dibromo Adducts

The 2-hydroxy-3-oxoglycal derivatives 5a, 5b, and 11 - acetyl-, pivaloyl-, and methyl-protected, respectively, at their hydroxylic functions - are synthesized by oxidation with dimethyl sulfoxide/acetic anhydride or chlorosulfonyl isocyanate of the corresponding 1-O-acylglucopyranoses 3a, 3b, and 9, respectively, each containing a free 3-hydroxy group.Only in the case of the acetyl derivative 3a the oxidation is immediately followed by the elimination of the 1-acetyloxy substituent.In contrast, the oxidation of both the pivaloyl derivative 3b and the methyl derivative9 yields mainly the corresponding 3-ulose 4 and 10, respectively.Here, the elimination of the 1-acyloxy group must be completed by diazabicycloundecene (DBU). - Bromine is added stereoselectively to the hex-1-enopyran-3-uloses 5a, 5b, and 11 forming the D-ribo-configurated 1,2-dibromides 13/14.Moreover, in the cases of the pivaloyl and the methyl derivates only theα anomers 13 are formed.The configurations of the adducts have been estimated by means of NMR and CD spectra.