95189-55-2

Upstream product

• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 544-97-8 dimethyl zinc(II) 
• 62774-37-2 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranoside 
• 116417-39-1 butyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 116417-40-4 butyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside 
• 136742-92-2 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1,1-dichloro-D-gluco-hept-1-enitol 
• 140658-53-3 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C--α-D-glucopyranose 
• 1193390-71-4 (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(bis(phenylsulfonyl)methyl)tetrahydro-2H-pyran 
• 187226-51-3 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-mannopyranoside 
• 352020-73-6 (2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methyltetrahydro-2H-pyran-2-ol 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 137344-41-3 3,4,5,7-Tetra-O-benzyl-1-deoxy-D-gluco-2-heptulopyranose 
• 140658-54-4 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-C-<(methylthio)methyl>-α-D-glucopyranose 

Relevant academic research and scientific papers

A Mitsunobu route to C-glycosides

C-Glycosides were successfully prepared via dehydrative alkylation under Mitsunobu conditions, using substituted sulfonyl methanes as nucleophiles. The materials prepared were converted to useful C-glycoside intermediates. An application of this approach

An efficient synthesis of β-C-glycosides based on the conformational restriction strategy: Lewis acid promoted silane reduction of the anomeric position with complete stereoselectivity

(Chemical Equation Presented) The reduction of glyconolactols having an anomeric carbon substituent by Et3SiH/TMSOTf proceeded with complete stereoselectivity to produce the corresponding β-C-glycosides when the substrates were conformationally restricted in the 4C 1-chair form by a 3,4-O-cyclic diketal or a 4,6-O-benzylidene protecting group. Thus, the efficient construction of β-C-glycosides was achieved on the basis of the conformation restriction strategy.

Unusual Behaviour of Some γ- and δ-Lactones Towards Dichloromethylenation using Tris(dimethylamino)phosphine-Tetrachloromethane

Lactones derived from D-glucose, D-mannose and L-ascorbic acid reacted unexpectedly with tris(dimethylamino)phosphine-tetrachloromethane to give, respectively, dichloroalkene, anomeric vinyl chloride or acyl chloride; this behaviour supports an ionic mech

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.

ORGANOMETALLICS IN ORGANIC SYNTHESIS. APPLICATIONS OF A NEW DIORGANOZINC REACTION TO THE SYNTHESIS OF C-GLYCOSYL COMPOUNDS WITH EVIDENCE FOR AN OXONIUM-ION MECHANISM

The mechanistic and stereochemical features of a new organozinc-based substitution process 1,R2)-SPh + R32Zn --> heteroatom-C-(R1,R2,R3)>, first discovered during a total synthesis of the alkaloid mycotoxin α-cyclopiazonic acid, are described.Phenyl thioglycosides were valuable substrates in studying the nature of this reaction process.Since these sulfur compounds are converted into C-glycosyl compounds with some degree of stereoselectivity, the organozinc chemistry does provide a new entry to these biologically active substances.