90820-62-5

Upstream product

• 32252-03-2 (-)-1'-deoxy-1'-phenyl-β-D-ribofuranose 
• 108-24-7 acetic anhydride 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 
• 138511-91-8 2',3',5'-tri-O-benzyl-1'-deoxy-1'-phenyl-β-D-ribofuranose 
• 138385-32-7 (R)-2,3,5-tri-O-benzyl-1-C-phenyl-D-ribitol 
• 105499-44-3 2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride 
• 100-58-3 phenylmagnesium bromide 
• 55057-34-6 2,3,5-tri-O-acetyl-α-D-ribofuranosyl bromide 
• 53402-29-2 2,3,5-tri-O-acetyl-β-D-ribofuranosyl chloride 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 

Relevant academic research and scientific papers

Synthesis of Aryl C-Glycosides via Iron-Catalyzed Cross Coupling of Halosugars: Stereoselective Anomeric Arylation of Glycosyl Radicals

We have developed a novel diastereoselective iron-catalyzed cross-coupling reaction of various glycosyl halides with aryl metal reagents for the efficient synthesis of aryl C-glycosides, which are of significant pharmaceutical interest due to their biological activities and resistance toward metabolic degradation. A variety of aryl, heteroaryl, and vinyl metal reagents can be cross-coupled with glycosyl halides in high yields in the presence of a well-defined iron complex, composed of iron(II) chloride and a bulky bisphosphine ligand, TMS-SciOPP. The chemoselective nature of the reaction allows the use of synthetically versatile acetyl-protected glycosyl donors and the incorporation of various functional groups on the aryl moieties, producing a diverse array of aryl C-glycosides, including Canagliflozin, an inhibitor of sodium-glucose cotransporter 2 (SGLT2), and a prevailing diabetes drug. The cross-coupling reaction proceeds via generation and stereoselective trapping of glycosyl radical intermediates, representing a rare example of highly stereoselective carbon-carbon bond formation based on iron catalysis. Radical probe experiments using 3,4,6-tri-O-acetyl-2-O-allyl-α-d-glucopyranosyl bromide (8) and 6-bromo-1-hexene (10) confirm the generation and intermediacy of the corresponding glycosyl radicals. Density functional theory (DFT) calculations reveal that the observed anomeric diastereoselectivity is attributable to the relative stability of the conformers of glycosyl radical intermediates. The present cross-coupling reaction demonstrates the potential of iron-catalyzed stereo- and chemoselective carbon-carbon bond formation in the synthesis of bioactive compounds of certain structural complexity.

Cobalt-catalyzed diastereoselective synthesis of C-furanosides. total synthesis of (-)-isoaltholactone

An array of C-aryl and C-vinyl furanosides were prepared in good yields and diastereoselectivities from C-halogeno furanosides either with aryl Grignard or with vinyl Grignard using the convenient Co(acac)3/TMEDA catalytic system. This method i

Diastereoselective Ni-catalyzed Negishi cross-coupling approach to saturated, fully oxygenated C-alkyl and C-aryl glycosides

A Ni-catalyzed Negishi cross-coupling approach to C-glycosides is described with an emphasis on C-aryl glycosides. The combination of NiCl 2/PyBox in N,N′-dimethylimidazolidinone (DMI) enabled the synthesis of C-alkyl glycosides under mild reaction conditions. Moderate yields and β-selectivities were obtained for C-glucosides, and good yields and high α-selectivities were the norm for C-mannosides. For C-aryl glycosides, reactions employing Ni(COD)2/tBu-Terpy in N,N-dimethylformamide (DMF) were typically high yielding and provided C-glucosides with high β-selectivities (1:>10 α:β) and C-mannosides in moderate α-selectivities (3:1 α:β); α-C-aryl glycosides could be obtained by the combination of Ni(COD) 2/PyBox in DMF (>20:1 α:β). The collective studies suggest that stereochemical control of the C-glycosides is dependent on the substrate and catalysts combination. The Negishi protocol displays excellent functional group tolerance, as demonstrated by its use in the first total synthesis of the natural product salmochelin SX.

Synthesis and cytotoxic activity of C-glycosidic nicotinamide riboside analogues

The C-glycosidic nicotinamide riboside analogue (2) was prepared by reaction of ribonolactone 24 with the lithiated oxazoline 19 followed by triethylsilane reduction to 26 and deprotection. Selective phosphorylation to the pseudonucleotide 34 was effected