352432-46-3

Upstream product

• 1769-00-2 Pentakis-O-(trimethylsilyl)-D-glucose 
• 492-62-6 alpha-D-glucopyranose 
• 1769-00-2 1,2,3,4,6-penta-O-trimethylsilyl-α-D-glucopyranose 
• 2280-44-6 D-Glucose 

Downstream Products

• 497-76-7 4-hydroxyphenyl α-D-glucopyranoside 

Relevant academic research and scientific papers

New Disaccharide-Based Ether Lipids as SK3 Ion Channel Inhibitors

The SK3 potassium channel is involved in the development of bone metastasis and in the settlement of cancer cells in Ca2+-rich environments. Ohmline, which is a lactose-based glycero-ether lipid, is a lead compound that decreases SK3 channel activity and consequently limits the migration of SK3-expressing cells. Herein we report the synthesis of three new ohmline analogues in which the connection of the disaccharide moieties (1→6 versus 1→4) and the stereochemistry of the glycosyl linkage was studied. Compound 2 [3-(hexadecyloxy)-2-methoxypropyl-6-O-α-d-glucopyranosyl-β-d-galactopyranoside], which possesses an α-glucopyranosyl-(1→6)-β-galactopyranosyl moiety, was found to decrease SK3 current amplitude (70 % inhibition at 10 μm), displace SK3 protein outside caveolae, and decrease constitutive Ca2+entry (50 % inhibition at 300 nm) and SK3-dependent cell migration (30 % at 300 nm) at a level close to that of the benchmark compound ohmline. Compound 2, which decreases the activity of SK3 channel (but not SK2 channel), is a new drug candidate to reduce cancer cell migration and to prevent bone metastasis.

Synthesis of oligosaccharides using per-O-trimethylsilyl-glycosyl iodides as glycosyl donor

Trimethylsilyl (TMS) protecting group has been found to be very useful for the simultaneous protection of both the glycosyl donor- and the acceptor-substrates in oligosaccharide synthesis. Thus, while the per-O-trimethylsilylated glycosyl iodides served a

Synthesis and structural characterization of three unique helicobacter pylori a-cholesteryl phosphatidyl glucosides

Steryl glycosides produced by bacteria play important biological roles in the evasion and modulation of host immunity. Step-economical syntheses of three cholesteryl-6-Ophosphatidyl-α-d-glucopyranosides (αCPG) unique to Helicobacter pylori have been achie

β-Selective C-Glycosylation and its Application in the Synthesis of Scleropentaside A

C-Glycosides are carbohydrates that bear a C?C bond to an aglycon at the anomeric center. Due to their high stability towards chemical and enzymatic hydrolysis, these compounds are widely used as carbohydrate mimics in drug development. Herein, we report a general and exclusively β-selective method for the synthesis of a naturally abundant acyl-C-glycosidic structural motif first found in the scleropentaside natural product family. A Corey–Seebach umpolung reaction as the key step in the synthesis of scleropentaside A and analogues enables the β-selective construction of the anomeric C?C bond starting from unprotected carbohydrates in only four steps. The one-pot approach is highly atom-efficient and avoids the use of toxic heavy metals.

Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-O-silylated Mono- and Disaccharides

Reported herein is a general method for the efficient syntheses of a variety of β-cyano glycosides through the activation of per-O-trimethylsilyl glycosides with TMSI to form α-glycosyl iodides, which undergo SN2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)6 in THF/H2O to give the corresponding aminomethyl glycosides.

A palladium-catalyzed approach to allenic aromatic ethers and first total synthesis of terricollene A

A palladium-catalyzed C-O bond formation reaction between phenols and allenylic carbonates to give 2,3-allenic aromatic ethers with decent to excellent yields under mild reaction conditions has been described. A variety of synthetically useful functional

Expeditious Synthesis of Ieodoglucomides A and B from the Marine-Derived Bacterium Bacillus licheniformis

We report the total synthesis of ieodoglucomides A and B. The key steps of the synthesis are a glycosyl-iodide-mediated β-stereoselective glycosylation without neighbouring-group participation, a regioselective acylation, and a Grubbs cross-metathesis reaction. The short and efficient synthesis involves 11 steps, with 38–40 % overall yield.

Synthesis and biological activity of α-glucosyl C24:0 and C20:2 ceramides

α-Glucosyl ceramides 4 and 5 have been synthesised and evaluated for their ability to stimulate the activation and expansion of human iNKT cells. The key challenge in the synthesis of both target molecules was the stereoselective synthesis of the α-glycos

ONE-POT SYNTHESIS OF ALPHA/BETA-O-GLYCOLIPIDS

The present invention provides a one-pot method of preparing an unprotected α-O-glycolipid. The first step involves contacting a protected α-iodo sugar with a catalyst and a lipid comprising a hydroxy group, under conditions sufficient to prepare a protected α- O-glycolipid. The second step involves deprotecting the protected α-O-glycolipid under conditions sufficient to prepare the unprotected α-O-glycolipid, wherein the contacting and deprotecting steps are performed in a single vessel. The present invention also provides a one-pot method of preparing an unprotected β-O-glycolipid following the steps for the preparation of the unprotected α-O-glycolipid.