474382-55-3

Upstream product

• 76375-66-1 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 193953-69-4 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl diethyl phosphite 

Downstream Products

• 130050-86-1 methyl (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->2)-3-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Environmentally benign and stereoselective formation of β-O-glycosidic linkages using benzyl-protected glucopyranosyl phosphite and montmorillonite K-10

An environmentally benign and highly stereoselective β-glucopyranosylation without neighboring group participation has been developed employing benzyl-protected glucopyranosyl diethyl phosphite as a glycosyl donor and montmorillonite K-10 as an activator.

Visible-light-promoted 3,5-dimethoxyphenyl glycoside activation and glycosylation

A new glycosylation method promoted by visible light with 3,5-dimethoxyphenyl glycoside as the donor was developed. This protocol delivers bothO-glycosides andN-glycosides in moderate to excellent yields using a wide range ofO-nucleophiles and nucleobases as the glycosyl acceptors.

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.

Stereoselective Koenigs–Knorr Glycosylation Catalyzed by Urea

A stereoselective Koenigs–Knorr glycosylation reaction under the catalysis of urea is described. This method is characterized by urea-mediated hydrogen-bond activation and subsequent glycosylation with glycosyl chlorides or bromides. Excellent yields and high anomeric selectivity can be achieved in most cases. Moreover, the low α-stereoselectivity of glycosylations observed when using perbenzylated glucosyl donors can be greatly improved by the addition of tri-(2,4,6-trimethoxyphenyl)phosphine (TTMPP).

An Alternative Reaction Course in O-Glycosidation with O-Glycosyl Trichloroacetimidates as Glycosyl Donors and Lewis Acidic Metal Salts as Catalyst: Acid-Base Catalysis with Gold Chloride-Glycosyl Acceptor Adducts

Gold(III) chloride as catalyst for O-glycosyl trichloroacetimidate activation revealed low affinity to the glycosyl donor but high affinity to the hydroxy group of the acceptor alcohol moiety, thus leading to catalyst-acceptor adduct formation. Charge sep

Stereoselective synthesis of glycosides using (salen)Co catalysts as promoters

The use of (salen)Co catalysts as a new class of bench-stable stereoselective glycosylation promoters of trichloroacetimidate glycosyl donors at room temperature is described. The conditions are practical and do not require the use of molecular sieves wit

Environmentally benign β-stereoselective glycosidations of glycosyl phosphites using a reusable heterogeneous solid acid, montmorillonite K-10

Environmentally benign and stereoselective β-glycosidations of glycopyranosyl phosphites and alcohols using a reusable heterogeneous solid acid, montmorillonite K-10, as an activator have been developed. By these glycosidations, β-gluco-, 2-deoxy-β-gluco-

Efficient activation of glycosyl N-(phenyl)trifluoroacetimidate donors with ytterbium(III) triflate in the glycosylation reaction

The mild, moisture-stable and cheap catalyst Yb(OTf)3 activates glycosyl N-(phenyl)trifluoroacetimidates in the stereoselective synthesis of 1,2-trans and 1,2-cis glycosides. A suitable choice of the reaction solvent led to good yields and stereoselectivity ratios. The protocol was successfully applied to acceptors and donors both exhibiting a wide range of reactivity.