38714-70-4

Upstream product

• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 108-24-7 acetic anhydride 
• 28538-11-6 (1S)-1,5-anhydro-1-(4-methoxyphenyl)-D-glucitol 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 100-66-3 methoxybenzene 
• 93414-73-4 2,3,4,6-tetra-O-benzyl-1-deoxy-1-(4-methoxyphenyl)-β-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 696-62-8 para-iodoanisole 
• 604-69-3 β-D-glucose pentaacetate 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 604-68-2 α-D-glucopyranose peracetylate 
• 119529-67-8 4-<(1R,2R,3S,4R,5R)-2,3,4,6-Tetrabenzyloxy-1-hydroxy-5-(methoxymethoxy)hexyl>anisol 

Downstream Products

• 28538-11-6 (1S)-1,5-anhydro-1-(4-methoxyphenyl)-D-glucitol 
• 261955-99-1 4-(2,3,4-tri-O-benzyl-6-desoxy-β-D-xylo-hex-5-enopyranosyl)anisole 
• 891783-10-1 4-(2,3,4-tri-O-acetyl-6-desoxy-6-iodo-β-D-glucopyranosyl)anisole 
• 891783-11-2 4-(2,3,4-tri-O-acetyl-6-desoxy-β-D-xylo-hex-5-enopyranosyl)anisole 

Relevant academic research and scientific papers

Stereoselective Preparation of C-Aryl Glycosides via Visible-Light-Induced Nickel-Catalyzed Reductive Cross-Coupling of Glycosyl Chlorides and Aryl Bromides

A nickel-catalyzed cross-coupling reaction of glycosyl chlorides with aryl bromides has been developed. The reaction proceeds smoothly under visible-light irradiation and features the use of bench-stable glycosyl chlorides, allowing the highly stereoselective synthesis of C-aryl glycosides. (Figure presented.).

Cyanide-Free Synthesis of Glycosyl Carboxylic Acids and Application for the Synthesis of Scleropentaside A

We have developed a cyanide-free strategy for the synthesis of glycosyl carboxylic acids, which can provide 1,2-trans or 1,2-cis glycosyl carboxylic acids and is compatible with common protecting groups. The synthetic utility was demonstrated by the synth

Nickel-catalyzed reductive coupling of glucosyl halides with aryl/vinyl halides enabling β-selective preparation of C-aryl/vinyl glucosides

This work describes stereoselective preparation of β-C-aryl/vinyl glucosides via mild Ni-catalyzed reductive arylation and vinylation of C1-glucosyl halides with aryl and vinyl halides. A broad range of aryl halides and vinyl halides were employed to yield C-aryl/vinyl glucosides in 42%–93% yields. Good to excellent β-selectivities were obtained for C-glucosides by using tridentate ligand.

C- aryl glycoside compound and synthesis method thereof

The invention relates to a C-aryl glycoside compound and a synthesis method thereof. A structural formula of the compound is shown in the description, wherein R is H, acetyl, methyl formate group, NHBoc or 4-methoxy; basic reaction takes glycosyl bromide and aryl iodine (bromine) as a substrate, and reaction is gently performed for 6-12 hours under icy-water bath or normal temperature under actions of a catalyst, a ligand, a reducer and an additive, so that the C-aryl glycoside compound is obtained. The catalyst metal is relatively cheap, raw materials are simple and easily available, the reaction is moderate, one-step reaction is performed, steps are simple, operations are safe, and the yield is relatively high, so that stereoselectivity is relatively good.

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.

Diastereoselective metal-catalyzed synthesis of C-aryl and C-vinyl glycosides

Cobalt, the catalyst of choice: The diastereoselective cobalt-catalyzed cross-coupling of 1-bromo glycosides and aryl or vinyl Grignard reagents is described. A convenient and inexpensive catalyst, [Co(acac)3]/tmeda (acac=acetylacetonate, tmeda=N,N'-tetramethylethylenediamine), gives full α selectivity in the mannose and galactose series, and an α selectivity in the glucose series with α/β ratios of 1.3:1-3:1. Copyright

Diastereoselective metal-catalyzed synthesis of C-aryl and C-vinyl glycosides

Cobalt, the catalyst of choice: The diastereoselective cobalt-catalyzed cross-coupling of 1-bromo glycosides and aryl or vinyl Grignard reagents is described. A convenient and inexpensive catalyst, [Co(acac)3]/tmeda (acac=acetylacetonate, tmeda=N,N'-tetramethylethylenediamine), gives full α selectivity in the mannose and galactose series, and an α selectivity in the glucose series with α/β ratios of 1.3:1-3:1. Copyright

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.

Remarkable β-selectivity in the synthesis of β-1-C- arylglucosides: Stereoselective reduction of acetyl-protected methyl 1-C-arylglucosides without acetoxy-group participation

(Chemical Equation Presented) An efficient and practical process to generate β-C-arylglucoside derivatives was achieved. The process described involves Lewis acid mediated ionic reduction of a peracetylated 1-C-aryl methyl glucoside derived from the addit

Triisobutylaluminium (TIBAL) promoted rearrangement of C-glycosides

Triisobutylaluminium-promoted rearrangement of unsaturated glycosides containing electron-donating aglycons, such as C-aryl glycosides, provides direct access to highly functionalised cyclohexane derivatives.