111425-48-0

Upstream product

• 108-98-5 thiophenol 
• 2873-29-2 D-glucal triacetate 
• 882-33-7 diphenyldisulfane 
• 69534-73-2 3,4,6-O-tri-O-acetyl-D-glucal 

Downstream Products

• 136787-38-7 styryl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 136787-39-8 styryl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside 
• 136787-42-3 4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-3-C-benzoylmethyl-D-ribo-hex-1-enitol 
• 136787-42-3 4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-3-C-benzoylmethyl-D-arabino-hex-1-enitol 
• 111425-50-4 phenyl 1-thio-4,6-O-isopropylidene-α-D-erythro-hex-2-enopyranoside 
• 5987-33-7 4,6-O-benzylidene-D-allal 
• 134756-58-4 C₁₉H₁₈O₃S 
• 1279711-50-0 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1R-deutero-D-altropyranose 
• 13265-84-4 1,2-didehydrodideoxyallose 
• 1393354-13-6 C₂₇H₂₉FO₅ 
• 1393354-12-5 C₂₇H₂₉FO₅ 
• 1393354-10-3 C₂₇H₂₉FO₅ 
• 1393354-09-0 C₂₇H₂₉FO₅ 
• 55628-54-1 (2R,3S,4S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyran 

Relevant academic research and scientific papers

Niobium(V) chloride catalyzed microwave assisted synthesis of 2,3-unsaturated O-glycosides by the Ferrier reaction

NbCl5 catalyzes the Ferrier reaction of per-O-acetylated glycals with primary, secondary, allylic, benzylic and monosaccharide alcohols to give 2,3-unsaturated α-glycosides in short reaction times under microwave irradiation conditions.

Highly stereoselective synthesis of pseudoglycals via Yb(OTf)3 catalyzed Ferrier glycosylation

The reaction of tri-O-acetyl-D-glucal with various alcohols and thiols was effectively promoted by a catalytic amount of Yb(OTf)3 to produce a variety of pseudoglycals via Ferrier rearrangement in excellent yields and anomeric selectivity.

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.

Ferrier rearrangement catalyzed by HClO4-SiO2: Synthesis of 2,3-unsaturated glycopyranosides

Alkyl 2,3-unsaturated glycopyranosides have been prepared by the Ferrier rearrangement of acetyl protected glycals catalyzed by HClO4-SiO 2. Operational simplicity, use of economically convenient catalyst, mild reaction conditions, high yields, short reaction times are the key features of this protocol.

FeCl3.6H2O/C: An Efficient and Recyclable Catalyst for the Synthesis of 2,3-Unsaturated O-and S-Glycosides

A novel method for synthesizing 2,3-unsaturated glycosides has been developed using a handy and eco-friendly immobilized catalyst, FeCl3.6H2O/C. A series of 2,3-unsaturated O-and S-glycosides were obtained for bioassay from corresponding 3,4,6-tri-O-acetyl-D-glucal and D-galactal in good to excellent yields (56%-99%) and high anomeric selectivity (α/β = 7:1 to >19:1). Furthermore, the catalyst was efficient on gram-scale reactions and recyclable for at least three times.

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.

Photo amidoglycosylation of an allal azidoformate. Synthesis of beta-2-amido allopyranosides.

[figure: see text] Photolysis of an allal C-3 azidoformate provoked intramolecular nitrene insertion into the glycal C=C unit and allowed direct incorporation of alcohol nucleophiles as beta-disposed substituents at C-1. The 2-amido allopyranoside product

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.