13231-13-5

Basic information

• Product Name: (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene
• Synonyms: (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene
• CAS NO: 13231-13-5
• Molecular Weight: 408.405
• Mol File: 13231-13-5.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene(13231-13-5)
• EPA Substance Registry System: (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene(13231-13-5)

Safety Data

• Hazardous Substances Data: 13231-13-5(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 125412-60-4 C-[4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]benzene 
• 13242-53-0 acetobromomannose 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 591-50-4 iodobenzene 
• 2674-04-6 diphenyl cadmium 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 108-88-3 toluene 
• 23402-69-9 lithium diphenylcuprate 
• 3867-86-5 Brigl's anhydride 
• 5627-22-5 (2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triol 
• 7446-70-0 aluminium trichloride 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 71-43-2 benzene 

Downstream Products

• 882302-30-9 (2R,3S,4R,4aS,10aR)-6,6,8,8-Tetraisopropyl-2-phenyl-hexahydro-1,5,7,9-tetraoxa-6,8-disila-benzocyclooctene-3,4-diol 
• 28836-04-6 1-(β-D-glucopyranosyl)-4-nitrobenzene 
• 119926-29-3 (2R,3R,4R,5S,6S)-benzoic acid 3,4,5-tribenzoyloxy-6-phenyltetrahydropyran-2-ylmethyl ester 
• 511274-75-2 Hept-6-enoic acid (2R,3R,4R,5S,6S)-2-hept-6-enoyloxymethyl-4,5-dimethoxy-6-phenyl-tetrahydro-pyran-3-yl ester 
• 511274-73-0 Pent-4-enoic acid (2R,3R,4R,5S,6S)-4,5-dimethoxy-2-pent-4-enoyloxymethyl-6-phenyl-tetrahydro-pyran-3-yl ester 
• 511274-33-2 (E)-(2S,3S,4R,4aR,15aR)-3,4-Dimethoxy-2-phenyl-2,3,4,4a,7,8,11,12,15,15a-decahydro-1,5,14-trioxa-benzocyclotridecene-6,13-dione 
• 511274-72-9 (2R,3R,4S,5S,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenyl-tetrahydro-pyran-3-ol 
• 261955-96-8 (2,3,4-tri-O-benzyl-6-desoxy-β-D-xylo-hex-5-enopyranosyl)benzene 
• 891783-07-6 (2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-glucopyranosyl)benzene 
• 891783-08-7 (2,3,4-tri-O-acetyl-6-desoxy-6-iodo-β-D-xylo-hex-5-enopyranosyl)benzene 
• 727416-79-7 (2R,4aR,6S,7R,8R,8aS)-6-Phenyl-2-(4-trifluoromethyl-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 850313-80-3 (2R,4aR,6S,7R,8R,8aS)-2-Biphenyl-4-yl-6-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 

Relevant articles and documents

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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.).

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.

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.