286410-13-7

Upstream product

• 108-98-5 thiophenol 
• 2873-29-2 D-glucal triacetate 
• 4098-06-0 triacetyl-D-galactal 
• 882-33-7 diphenyldisulfane 
• 125654-35-5 phenylthio-6-O-tert-butyldimethylsilyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 
• 69534-73-2 3,4,6-O-tri-O-acetyl-D-glucal 

Downstream Products

• 134756-58-4 C₁₉H₁₈O₃S 
• 1393354-13-6 C₂₇H₂₉FO₅ 
• 1393354-12-5 C₂₇H₂₉FO₅ 
• 1393354-10-3 C₂₇H₂₉FO₅ 
• 1393354-09-0 C₂₇H₂₉FO₅ 
• 125848-20-6 phenyl 2,3-dideoxy-1-thio-6-O-tosyl-α-D-threo-hex-2-enopyranoside 
• 1279711-65-7 C₂₇H₂₈O₅ 
• 1279711-66-8 C₂₀H₂₀O₅ 
• 69247-23-0 6-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 3427-20-1 methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 
• 125848-22-8 (2R,3S,6R)-2-Methyl-3-methylsulfanyl-6-phenylsulfanyl-3,6-dihydro-2H-pyran 

Relevant academic research and scientific papers

Synthesis of 2,3-unsaturated thioglycopyranosides mediated by lithium tetrafluoroborate

Treatment of tri-O acetyl-D-glucal 1 with diverse thiols 2-7 in the presence of LiBF4 in CH3CN, furnished aryl/alkyl 2,3-unsaturated thioglycopyranosides 8-13 (56-72%).

Azomethine ylide cycloaddition of 2-C-formyl glycals with α-amino acids for the synthesis of substituted pyrroles

A novel strategy has been devised for the synthesis of pyrrole based acyclo-C-nucleosides, in particular an open-chain sugar substituted pyrrole derivatives by means of the condensation of 2-C-formyl glycals with α-amino acids through an intramolecular azomethine cycloaddition under thermal conditions. The use of cyclic α-amino acids provides the corresponding bicyclic pyrrole derivatives. This is a first report on the synthesis of pyrrole based acyclo-C-nucleosides. 2009 Elsevier Ltd. All rights reserved.

Site-specific synthesis of 3-Se-1,2-unsaturated glycosides with R-Se-Se-R as the nucleophile precursors promoted by InCl3/Hf(OTf)4

By using Hf(OTf)4 as the catalyst, a series of 3-Se 1,2-unsaturated glucosides have been synthesized site-specifically from tri-O-acetyl-D-glucal, 3,4-di-O-acetyl-L-rhamnal or 2,4,6-tri-O-benzyl-D-glucal with alkyl(aryl) hydroselenides as the nucleophile precursors in good yield.

Synthesis of 3-S- and 3-Se-glycals by using R-S-S-R and R-Se-Se-R as the nucleophile precursors promoted by Hf(OTf)4 and the temperature-dependent formation of the above-mentioned 3-S- and 3-Se products

By using Hf(OTf)4 as the catalyst, under certain conditions, reaction of tri-O-acetyl-D-glucal and ((2R, 3S)-3-acetoxy-2,3-dihydrofuran-2-yl)methyl acetate with alkyl(aryl) bisulfide/alkyl(aryl) biselenide as nucleophile precursor leads to temperature-dependent formation of C-1-S/Se and C-3-S/Se product. A temperature-dependent profile of the yield of these two products is given.

Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- And S-linked glycosides

A convenient protocol was developed for the synthesis of 2,3-unsaturated C-, O-, N- and S-linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement. Using this protocol, D-glucals and L-rhamnals reacted with various C-, O-, N- and S-nucleophiles to give a wide range of glycosides in up to 98% yields with mainly α-anomeric selectivity. The perflurophenylboronic acid successfully catalyzed a wide range of substrates (both glucals and nucleophiles) under very mild reaction conditions.

Glycal Metallanitrenes for 2-Amino Sugar Synthesis: Amidoglycosylation of Gulal-, Allal-, Glucal-, and Galactal 3-Carbamates

The rhodium(II)-catalyzed oxidative cyclization of glycal 3-carbamates with in situ incorporation of an alcohol nucleophile at the anomeric position provides access to a range of 2-amino sugars having 1,2-trans-2,3-cis stereochemistry, a structural motif present in compounds of medicinal and biological significance such as the streptothricin group of antibiotics and the Chitinase inhibitor allosamidin. All of the diastereomeric d-glycal 3-carbamates have been investigated, revealing significant differences in anomeric stereoselectivity depending on substrate stereochemistry and protecting groups. In addition, some substrates were prone to forming C3-oxidized dihydropyranone byproducts under the reaction conditions. Allal- and gulal 3-carbamates provided uniformly high stereo- and chemoselectivity, while for glucal substrates, acyclic, electron-withdrawing protecting groups at the 4O and 6O positions were required. Galactal 3-carbamates have been the most challenging substrates; formation of their amidoglycosylation products is most effective with an electron-withdrawing 6O-Ts substituent and a sterically demanding 4O-TBS group. These results suggest a mechanism whereby conformational and electronic factors determine the partitioning of an intermediate acyl nitrenoid between alkene addition, leading to amidoglycosylation, and C3-H insertion, providing the dihydropyranone byproduct. Along the amidoglycosylation pathway, high anomeric selectivity results when a glycosyl aziridine intermediate is favored over an aziridine-opened oxocarbenium donor.

Hafnium(IV) triflate as a highly efficient catalyst for Ferrier rearrangement of O- and S-nucleophiles with glycals

A highly efficient method to afford 2,3-unsaturated glycosides was described. In the presence of Hafnium(IV) triflate, a variety of 2,3-unsaturated-O- and S-glycosides have been obtained by stereoselective glycosylation of 3,4,6-tri-O-acetyl-d-glucal and hexa-O-acetyl-d-lactal with various acceptors in good isolated yields.

Gd(OTf)3 catalyzed preparation of 2,3-unsaturated O-, S-, N-, and C-pyranosides from glycals by Ferrier Rearrangement

By using Gd(OTf)3 as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed by Ferrier Rearrangement. A series of 2,3-unsaturated O-, S-, N-, and C-glycosides were obtained from 3,4,6-tri-O-acetyl-d-glucal, 3,4,6-tri-O-benzyl-d-glucal, and 3,4-di-O-acetyl-l-rhamnal under mild reaction conditions in good yields and high anomeric selectivities.

Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst

In situ generated zirconium catalyst from a sacrificial zirconium anode was successfully applied to promote Ferrier rearrangement of 3,4,5-tri-O-acetyl-d-glucal and 6-deoxy-3,4-di-O-acetyl-l-glucal (3,4-di-O-acetyl-l-rhamnal) in the presence of three thiols and eleven thiophenols as nucleophiles. A simple constant current electrolysis (20 mA, 0.4 F mol-1) of an acetonitrile solution of lithium perchlorate (0.1 M) containing the corresponding glycal and S-nucleophiles, using a zirconium anode and a platinum cathode resulted in the successful synthesis of the corresponding 2,3-unsaturated peracetylated thioglycosides (with an average anomer ratio α/β=4.129 in the case of peracetylated d-glucal and 8.740 in the case of l-rhamnal). The same procedure proved to be appropriate in synthesizing dihydropyran derivatives ('C-glycosides') using allyltrimethylsilane as the nucleophile (only 'α-anomers' were obtained). All new compounds were fully characterized by spectral data, whereas single-crystal X-ray analysis was performed for two thioglycosides.

Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)-C(3) Unsaturated and α-d-Mannopyranosyl Sulfones

An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and α-d-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access α-d-mannopyranosyl sulfones in good yields with high regioselectivity.