30906-26-4

Upstream product

• 15681-48-8 lithium dimethylcuprate 
• 3867-86-5 Brigl's anhydride 
• 108-24-7 acetic anhydride 
• 917-54-4 methyllithium 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 23402-69-9 lithium diphenylcuprate 
• 74372-90-0 1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose 
• 108-86-1 bromobenzene 
• 352310-78-2 3,4,5,7,-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptose tosylhydrazone 

Relevant academic research and scientific papers

Pd-catalyzed coupling reactions of anhydro-aldose tosylhydrazones with aryl bromides to produce substituted exo-glycals

Palladium-catalyzed cross-couplings of O-peracylated and O-permethylated 2,6-anhydro-aldose tosylhydrazones with aryl halides were studied under thermic conditions in the presence of LiOtBu and phosphine ligands. The reactions gave the corresponding aryl substituted exo-glycals as mixtures of diastereomers in 11–75% yields. The transformations represent a new access to these types of glycomimetic compounds. The double bond of some aryl substituted exo-glycals was saturated to give good yields of benzylic C-glycosyl derivatives.

Reaction of organocuprate reagents with protected 1,2-anhydro sugars. Stereocontrolled synthesis of 2-deoxy-C-glycosyl compounds

The reaction of protected 1,2-anhydro-α-D-gluco- and β-D-manno-pyranoses with alkyl and phenyl organocuprates afforded the corresponding C-glycosyl compounds in acceptable to high yield. Complete stereocontrol was obtained, leading respectively to the β-D or the α-D anomer. With the perbenzylated manno derivative, deoxygenation at C-2 was achieved in high yield, affording 2-deoxy-α-D-C-glycosyl compounds.

Stereocontrolled Synthesis of C-Glycosides by Reaction of Organocuprates with Protected 1,2-Anhydro Sugars, and their Transformation into 2-Deoxy-C-glycosides

The reaction of protected 1,2-anhydro sugars with organocuprates provides a new stereocontrolled synthesis of C-glycosides, the deoxigenation of which affords 2-deoxy-C-glycosides in high yield.

Synthesis of C-Glucosides by Reactions of Glucosyl Halides with Organocuprates.

Lithium dimethylcuprate reacts with trans-2-chloro-6-methyltetrahydropyran (1) via nucleophilic substitution predominantly with inversion of configuration to afford cis-2,6-dimethyltetrahydropyran (2).Similarly, lithium dialkylcuprates displace protected α-glucosyl bromides (5) with inversion to afford the β-C-glucosides, β-1-alkyl-1,5-anhydroglucitols (6).In contrast, Grignard reagents gave mixtures of α- and β- glucosides 6 and 7, while organolithium reagents gave only elimination to 9.