41671-29-8

Upstream product

• 80667-82-9 1,2:3,4-di-O-isopropyliden-6-O-(trimethylsilyl)-α-D-galactopyranose 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 89025-46-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride 
• 144490-57-3 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-αβ-D-glucopyranoside 
• 96863-21-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate 
• 38768-84-2 Dibenzyl(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)phosphat 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 90357-89-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 
• 82300-58-1 dibezylphosphoryl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 942907-29-1 Imidazole-1-carboxylic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 

Relevant academic research and scientific papers

In(III) triflate-mediated solvent-free synthesis and activation of thioglycosides by ball milling and structural analysis of long chain alkyl thioglycosides by TEM and quantum chemical methods

Conventional solution-phase synthesis of thioglycosides from glycosyl acetates and thiols in the presence of In(III) triflate as reported for benzyl thioglucoside failed when applied to the synthesis of phenolic and alkyl thioglycosides. But, it was achieved in high efficiency and diastereospecificity with ease by solvent-free grinding in a ball mill. The acetates in turn were also obtained by the homogenization of free sugars with stoichiometric amounts of acetic anhydride and catalytic In(OTf)3 in the mill as neat products. Per-O-benzylated thioglycosides on grinding with an acceptor sugar in the presence of In(OTf)3 yield the corresponding O-glycosides efficiently. The latter in the case of a difficult secondary alcohol was nearly exclusive (>98%) in 1,2-cis-selectivity. In contrast, the conventional methods for this purpose require use of a coreagent such as NIS along with the Lewis acid to help generate the electrophilic species that actually is responsible for the activation of the thioglycoside donor in situ. The distinctly different self-assembling features of the peracetylated octadecyl 1-thio-α- and β-d-galactopyranosides observed by TEM could be rationalized by molecular modeling.

2-Diphenylphosphinonyl-acetyl as a Remote Directing Group for the Highly Stereoselective Synthesis of β-Glycosides

The configuration of the anomeric glycosidic linkages is crucial for maintaining the biological functions and activities of carbohydrate molecules. However, their stereochemistry control in glycosylation represents one of the most challenging tasks in car

A Mechanistic Probe into 1,2-cis Glycoside Formation Catalyzed by Phenanthroline and Further Expansion of Scope

Phenanthroline, a rigid and planar compound with two fused pyridine rings, has been used as a powerful ligand for metals and a binding agent for DNA/RNA. We discovered that phenanthroline could be used as a nucleophilic catalyst to efficiently access high

HEPARANASE INHIBITORS FOR TREATMENT OF DIABETES

Anti-heparanase compounds for the treatment of diabetes are described. The anti-heparanase compounds are high affinity, synthetic glycopolymers that result in minimal anticoagulant activity. Stereoselective fluorinated forms of these compounds are also pr

How do Various Reaction Parameters Influence Anomeric Selectivity in Chemical Glycosylation with Thioglycosides and NIS/TfOH Activation?

The reaction of glycosyl donor phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside with NIS/TfOH(cat.) was systematically studied under various reaction conditions. Neither the molecular sieve pore size nor amount of NIS activator was found to have a

Visible-light-induced photoacid catalysis: Application in glycosylation with: O -glycosyl trichloroacetimidates

The development of visible-light-induced photoacid catalyzed glycosylation is reported. The eosin Y and PhSSPh catalyst system is applied to realize glycosylation with different glycosyl donors upon light irradiation. The reaction shows a broad substrate

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.

A "traceless" Directing Group Enables Catalytic SN2 Glycosylation toward 1,2- cis-Glycopyranosides

Generally applicable and stereoselective formation of 1,2-cis-glycopyranosidic linkage remains a long sought after yet unmet goal in carbohydrate chemistry. This work advances a strategy to this challenge via stereoinversion at the anomeric position of 1,2-trans glycosyl ester donors. This SN2 glycosylation is enabled under gold catalysis by an oxazole-based directing group optimally tethered to a leaving group and achieved under mild catalytic conditions, in mostly excellent yields, and with good to outstanding selectivities. The strategy is also applied to the synthesis of oligosaccharides.

Diastereoselective sp3C-O Bond Formation via Visible Light-Induced, Copper-Catalyzed Cross-Couplings of Glycosyl Bromides with Aliphatic Alcohols

Copper-catalyzed cross-coupling reactions have become one of the most powerful methods for generating carbon-heteroatom bonds, an important framework of many organic molecules. However, copper-catalyzed C(sp3)-O cross-coupling of alkyl halides with alkyl

HEPARANASE INHIBITORS AND THEIR USE AS ANTI-CANCER COMPOUNDS

Anti-heparanase compounds for the treatment of cancer are described. The anti-heparanase compounds are high affinity, synthetic glycopolymers that result in minimal anticoagulant activity. Stereoselective fluorinated forms of these compounds are also prov