457931-46-3

Upstream product

• 83-87-4 D-Mannose pentaacetate 
• 530-26-7 D-Mannose 
• 106-45-6 para-thiocresol 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 211801-79-5 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 

Downstream Products

• 131531-70-9 4-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 755002-33-6 para-tolyl (R)-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 1157902-57-2 4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 1189021-70-2 4-methylphenyl 6-O-trityl-1-thio-α-D-mannopyranoside 
• 1320281-31-9 p-tolyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside 
• 1320281-32-0 methyl (p-tolyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranosyl uronate) 
• 942043-27-8 4-methylphenyl 2,3,4,6-tetra-O-trimethylsilyl-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

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.

From d-to l-Monosaccharide Derivatives via Photodecarboxylation-Alkylation

Photodecarboxylation-alkylation of conformationally locked monosaccharides leads to inversion of stereochemistry at C5. This allows the synthesis of l-sugars from their readily available d-counterparts. Via this strategy, methyl l-guloside was synthesized from methyl d-mannoside in 21% yield over six steps.

Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity

Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.

Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery

Glycosylated platinum(IV) complexes were synthesized as substrates for GLUTs and OCTs for the first time, and the cytotoxicity and detailed mechanism were determined in vitro and in vivo. Galactoside Pt(IV), glucoside Pt(IV), and mannoside Pt(IV) were highly cytotoxic and showed specific cancer-targeting properties in vitro and in vivo. Glycosylated platinum(IV) complexes 5, 6, 7, and 8 (IC50 0.24-3.97 μM) had better antitumor activity of nearly 166-fold higher than the positive controls cisplatin (1a), oxaliplatin (3a), and satraplatin (5a). The presence of a hexadecanoic chain allowed binding with human serum albumin (HSA) for drug delivery, which not only enhanced the stability of the inert platinum(IV) prodrugs but also decreased their reduction by reductants present in human whole blood. Their preferential accumulation in cancer cells compared to noncancerous cells (293T and 3T3 cells) suggested that they were potentially safe for clinical therapeutic use.

Convergent synthesis of oligosaccharides on the gram-scale using cetyl thioglycoside based on a hydrophobically assisted switching phase method

A hydrophobically assisted switching phase (HASP) method is an efficient strategy for the synthesis of carrier-loaded oligosaccharides. We improved this method by using cetyl thioglycoside as the carrier, which made it possible to use the synthetic oligosaccharide block directly as the donor. We applied this improved HASP method in the successful assembly of a gp120-associated nona-mannoside. Our results indicated that the HASP method is an efficient strategy for the synthesis of complex oligosaccharides and glycoconjugates.

Efficient assembly of oligomannosides using the hydrophobically assisted switching phase method

The hydrophobically assisted switching phase (HASP) method was applied in the assembly of oligomannosides. A new mannosyl donor with high reactivity was selected after a series of optimization studies, which was suitable for the synthesis of oligomannosides via the HASP method. The practicability of the HASP method towards the synthesis of branched oligosaccharides was explored and two branched penta-mannosides were assembled efficiently.

Acceptor Reactivity in the Total Synthesis of Alginate Fragments Containing α- L -Guluronic Acid and β- D -Mannuronic Acid

The total synthesis of mixed-sequence alginate oligosaccharides, featuring both β-D-mannuronic acid (M) and α-L-guluronic acid (G), is reported for the first time. A set of GM, GMG, GMGM, GMGMG, GMGMGM, GMGMGMG, and GMGGMG alginates was assembled using GM

In situ formation of β-glycosyl imidinium triflate from participating thioglycosyl donors: Elaboration to disarmed-armed iterative glycosylation

β-Glycosyl imidinium triflate is generated from participating thioglycoside donors for disarmed-armed iterative glycosylations and one-pot oligosaccharide synthesis.

Mannopyranosyl uronicaAcid donor reactivity

The reactivity of a variety of mannopyranosyl uronic acid donors was assessed in a set of competition experiments, in which two (S)-tolyl mannosyl donors were made to compete for a limited amount of promoter (NIS/TfOH). These experiments revealed that the reactivity of mannuronic acid donors is significantly higher than expected based on the electron-withdrawing capacity of the C-5 carboxylic acid ester function. A 4-O-acetyl-β-(S)-tolyl mannuronic acid donor was found to have similar reactivity as per-O-benzyl-α-(S)-tolyl mannose.

Stability of 5(6)-carboxyfluorescein in microwave-assisted synthesis of fluorescein-labelled O-dimannosylated peptides

Methodology for the efficient, automated and microwave-assisted Fmoc solid-phase synthesis of a 5(6)-carboxyfluorescein-labelled Lys(Dde)-Gly-Wang resin that can be further elongated through the lysine Nε amino group is described. Incorporation