116113-70-3

Upstream product

• 67-63-0 isopropyl alcohol 
• 343565-46-8 (BnO)4Gal-β-N-tosylcarbamate 
• 343565-47-9 (BnO)4Gal-β-N,N-(methyl)tosylcarbamate 
• 343565-48-0 (BnO)4Gal-β-N,N-(cyanomethyl)tosylcarbamate 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl fluoride 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 38184-10-0 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 3458-28-4 D-Mannose 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 23661-29-2 phenyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-glucopyranoside 

Relevant academic research and scientific papers

Remote Participation during Glycosylation Reactions of Galactose Building Blocks: Direct Evidence from Cryogenic Vibrational Spectroscopy

The stereoselective formation of 1,2-cis-glycosidic bonds is challenging. However, 1,2-cis-selectivity can be induced by remote participation of C4 or C6 ester groups. Reactions involving remote participation are believed to proceed via a key ionic intermediate, the glycosyl cation. Although mechanistic pathways were postulated many years ago, the structure of the reaction intermediates remained elusive owing to their short-lived nature. Herein, we unravel the structure of glycosyl cations involved in remote participation reactions via cryogenic vibrational spectroscopy and first principles theory. Acetyl groups at C4 ensure α-selective galactosylations by forming a covalent bond to the anomeric carbon in dioxolenium-type ions. Unexpectedly, also benzyl ether protecting groups can engage in remote participation and promote the stereoselective formation of 1,2-cis-glycosidic bonds.

Direct dehydrative glycosylation catalyzed by diphenylammonium triflate

Methods for direct dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.

Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, t

A visible light promoted O-glycosylation with glycosyl trichloroacetimidates using eosin Y as an organo photoacid

A photoacid catalyzed O-glycosylation of alcohols with glycosyl trichloroacetimidates in the presence of commercially available phenolic photoacids, fluorescein, 4′,5′-dibromo-fluorescein, and eosin Y under visible light irradiation by blue LEDs was devel

Visible light promoted method for constructing O-glycoside bonds

The invention discloses a visible light promoted method for constructing O-glycoside bonds. Glycosyl trichloroacetimidate is taken as a donor, and phenolic compounds are taken as a photocatalyst; a molecular sieve is added; and the O-glycoside bonds are g

N-benzoylglycine/thiourea cooperative catalyzed stereoselective O-glycosidation: Activation of O-glycosyl trichloroacetimidate donors

A new practical utility for β-stereoselective glycosylation via activation of O-glycosyl trichloroacetimidate donors using N-benzoylglycine/thiourea cooperative catalysis has been demonstrated. This method represents the first instance where amino acid derived N-benzoylglycine is used as a catalyst for O–glycosylation under mild reaction conditions at ambient temperature. NMR spectroscopy studies suggest that thiourea cocatalyst exhibit a cooperative behaviour that has a strong effect on the reaction rate, yield, and the β-selectivity.

An Unexpected FeCl 3/C-Catalyzed β-Stereoselective Glycosylation in the Presence of the C(2)-Benzyl Group

An efficient and completely β-stereoselective glycosylation that did not rely on neighboring group participation is described using 2-20 molpercent FeCl 3 /C as the catalyst and benzylated propargyl glycosides as the donors to reach yields up to 96percent under mild condition. With an octatomic-ring intermediate at the α-face of FeCl 3 /C with alkyne of propargyl glycosides, a panel of aglycones comprising aliphatic, alicyclic, unsaturated alcohols, halogenated alcohols, and phenols with different substitution were examined successfully for the exclusive β-stereoselective glycosylation reaction.

Gold(III)-Catalyzed Glycosylation using Phenylpropiolate Glycosides: Phenylpropiolic Acid, An Easily Separable and Reusable Leaving Group

An efficient and operationally simple gold(III)-catalyzed glycosylation protocol was developed using newly synthesized benchtop stable phenylpropiolate glycosyl (PPG) donors. Gold(III)-catalyzed activation of PPGs proceeds well with various carbohydrate a

Silver-catalyzed stereoselective formation of glycosides using glycosyl ynenoates as donors

A silver-catalyzed glycosylation reaction employing readily accessible and stable glycosyl ynenoates is developed. This reaction is mostly high yielding and exhibits varying levels of stereoinversion at the anomeric position. Compared to established and versatile Yu's gold catalysis, this chemistry features the use of substantially cheaper AgNTf2.

Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with glycosyl trichloroacetimidates under mild conditions

Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with trichloroacetimidate glycosyl donors is described. The reactions proceed efficiently with a wide range of acceptors, from sugar to nonsugar, under mild conditions in the presence of