65877-63-6

Usage

Chemical Properties

Amorphous White Powder

InChI:InChI=1/C13H18O6/c14-6-9-10(15)12(11(16)13(17)19-9)18-7-8-4-2-1-3-5-8/h1-5,9-17H,6-7H2/t9?,10-,11?,12+,13+/m1/s1

Upstream product

• 18006-25-2 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose diacetate 
• 84563-90-6 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-α-D-glucofuranose 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 18685-18-2 3-O-benzyl-1,2:5,6-di-O-isopropylidene-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 100-44-7 benzyl chloride 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 52560-18-6 3-O-Benzyl-1,2;5,6-di-O-cyclohexyliden-α-D-allofuranose 
• 18685-18-2 3-O-benzyl-1,2:5,6-di-O-isopropylidene-β-L-idofuranose 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 492-62-6 alpha-D-glucopyranose 
• 582-52-5 1,2:5,6-diacetone-D-glucose 

Downstream Products

• 187961-71-3 methyl 3-O-benzyl-β-D-mannopyranosyl-(1-4)-2,3,6-tri-O-benzoyl-α-D-glucopyranoside 
• 181228-44-4 1,2,4,6-tetra-O-benzoyl-3-O-benzyl-L-idopyranose 
• 42926-91-0 3-O-benzyl-1,6-anhydro-β-L-idopyranose 
• 334834-19-4 1,6-anhydro-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside 
• 87791-16-0 3-O-Benzyl-1,2,4,6-tetra-O-pivaloyl-β-D-glucopyranose 
• 27531-35-7 4-O-benzyl-D-glycero-D-gulo-heptono-1,5-lactone 
• 485812-46-2 3-O-benzyl-D-glucono-1,4-lactone 
• 39686-94-7 3-O-benzyl-1,2,4,6-tetra-O-acetyl-D-glucopyranose 
• 1393360-75-2 3-O-acetyl-2,6-anhydro-4-O-benzyl-5,7-O-p-methoxybenzylidene-1-O-triethylsilyl-D-glycero-D-gulo-heptitol 
• 1393360-91-2 4-O-acetyl-3,7-anhydro-5-O-benzyl-1,2-O-ditriethylsilyl-6,8-O-p-methoxybenzylidene-D-glycero-D-gulo-oct-1-enitol 
• 1393360-80-9 1-O-acetyl-2,6-anhydro-4-O-benzyl-5-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol 
• 1393360-81-0 3-O-acetyl-2,6-anhydro-4-O-benzyl-5-O-p-methoxybenzyl-1-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptitol 
• 1393360-85-4 3-O-benzyl-1,6-O-diacetyl-2-O-(p-methoxybenzyl)-4-O-tert-butyldiphenylsilyl-α-L-glucopyranose 
• 1393360-84-3 3-O-benzyl-1,6-O-diacetyl-2-O-(p-methoxybenzyl)-4-O-tert-butyldiphenylsilyl-β-L-glucopyranose 

Relevant academic research and scientific papers

Intercepted dehomologation of aldoses by N-heterocyclic carbene catalysis-a novel transformation in carbohydrate chemistry

The development of an N-heterocyclic carbene (NHC) catalysed intercepted dehomologation of aldoses is reported. The unique selectivity of NHCs for aldehydes is exploited in the complex context of reducing sugars. Examples of strong substrate governance for either intercepted dehomologation or a subsequent redox-lactonisation were identified and mechanistically understood. More importantly, it was shown that catalyst design allowed the tuning of the selectivity of the reaction with structurally unbiased starting materials towards either of the two scenarios.

ACIDIC DYSTROGLYCAN OLIGOSACCHARIDE COMPOUND AND METHOD FOR MAKING SAME

A synthetic dystroglycan oligosaccharide comprising Formula (I) wherein a repeating disaccharide motif consists of Glucuronic Acid (ClcA) and Xylose (Xyl) having a defined glycosyl connection GlcA-β-(1→3)-Xyl-α-(1→3)-GlcA; wherein either end of the synthetic dystroglycan oligosaccharide is conjugatable with chemical or biological vehicle or support; wherein the non-reducing terminal (II) is conjugatable with any oligosaccharides or groups that can modify a hydroxyl functionality; and wherein the reducing terminal is conjugatable with any tags, oligosaccharides or anything that can modify a hydroxyl functionality.

Preparation method of clostridium bolteae surface capsular polysaccharide structure derivative

The invention discloses a preparation method of a clostridium bolteae surface capsular polysaccharide structure derivative and belongs to the field of sugar chemistry. The preparation method comprisesthe following steps: taking glucose as a glycosyl donor to obtain a target beta-glycosidic bond; then successfully synthesizing a disaccharide building block through an oxidization-reduction glucoseC-2 site method; then synthesizing a target oligosaccharide structure which takes the disaccharide building block as a repeating unit, such as the gram-positive bacterium surface capsular polysaccharide structure derivative [arrow3]-alpha-D-Manp-(1arrow4)-beta-D-Rhap-(1arrow]5-Linker. A reducing end of decaose is connected with a connecting arm and is used for connecting protein to form a glycoconjugate for carrying out immunology researches. The method provided by the invention has the advantages of simplicity, time saving, labor saving and low cost; the obtained clostridium bolteae surface capsular polysaccharide structure derivative is possibly used for developing and preparing medicine related to autism.

Total synthesis of viscumneoside III of Viscum coloratum

The first total synthesis of viscumneoside III, a promising anti-angina pectoris dihydroflavone O-glycoside isolated from Viscum coloratum was described here. Trichloroaceti-midate was employed as the apiofuranosyl donor to construct the key building block of homoeriodictyol-7-O-β-D-apiosyl-(1 → 2)-β-D-glycoside (1). The longest linear sequence (from 2 to 1) in the synthetic route required thirteen steps and afforded the final product 1 with an overall yield of 6.3%.

A carbohydrate-based approach for the total synthesis of (-)-dinemasone B, (+)-4a-epi-dinemasone B, (-)-7-epi-dinemasone B, and (+)-4a,7-di-epi-dinemasone B

(-)-Dinemasone B was isolated by Krohn and co-workers from a culture of the endophytic fungus Dinemasporium strigosum and has shown promising antimicrobial activity. Described herein is the first total synthesis of (-)-dinemasone B, (+)-4a-epi-dinemasone B, (-)-7-epi-dinemasone B, and (+)-4a,7-di-epi-dinemasone B. Their absolute configurations were also determined. The developed synthesis features a stereoselective reduction of C-glycosidic ketone, lactonization, and E-olefination of aldehyde starting from d-glucose.

Synthesis of Fondaparinux: Modular synthesis investigation for heparin synthesis

The anti-thromboembolic pentasaccharide Fondaparinux was synthesized in 36 steps for the longest linear route, with 0.017% overall yield from d-glucose. Only three kinds of protecting groups were used for hydroxyl protection, Bn, Ac, and Bz, to accomplish this complex synthesis without decreasing the synthetic efficiency. Three l-idopyranosyl donors were investigated. Thioethyl glycoside is an efficient donor for l-idopyranosyl glycosylation with full α-selectivity, while l-idopyranosyl trichloroacetimidate resulted in poor α/β selectivity. A practical synthesis of key intermediate 1,6-anhydro-l-idopyranose 17 by H+/β-CD catalyst was developed.

Azetidine iminosugars from the cyclization of 3,5-Di- O -triflates of α-furanosides and of 2,4-Di- O -triflates of β-pyranosides derived from glucose

Primary amines with either 3,5-di-O-ditriflates of α-furanosides or 2,4-di-O-triflates of β-pyranosides form bicyclic azetidines in high yield.

Synthesis of orthogonally protected l-glucose, l-mannose, and l-galactose from d-glucose

An efficient route to orthogonally protected l-glucose, l-mannose, and l-galactose is described. Using the strategy to switch the functional groups at C1 and C5 of d-glucose, l-glucose is obtained via a key intermediate C-glycoside. Preparations of l-mannose and l-galactose derivatives from the orthogonally protected l-glucose were accomplished in good yields using the Lattrell-Dax method.

Development of carbohydrate-derived inhibitors of acid sphingomyelinase

The acid sphingomyelinase is an emerging drug target, especially for inflammatory lung diseases. Presently, there are no directly-acting potent inhibitors available for cell-based studies. The potent inhibitor phosphatidylinositol-3,5-bisphosphate (PtdIns3,5P2) is not only unsuited for cell culture studies, but also does not provide hints for further structural improvements. In the SAR study described here, we replaced the inositolphosphate moiety by a carbohydrate derivative and the phosphatidic acid residue by an alkylsulfone ester. The resulting compound is more active than its parent compound and offers new means for further structural modification.

The Glc2Man2-fragment of the N-glycan precursor - A novel ligand for the glycan-binding protein malectin?

The Glcα(1→3)Glcα(1→3)Manα(1→2)Man tetrasaccharide (Glc2Man2-fragment), a substructure of the natural N-glycan precursor, was synthesized. The interaction of this fragment with the protein malectin, a carbohydrate binding protein localized in the endoplasmatic reticulum, was investigated by 1H15N HSQC experiments and isothermal calorimetry. The chemical shift perturbations of nuclei in the protein's backbone caused by the binding of the Glc 2Man2-fragment to malectin suggest a binding mode like the known ligand nigerose. The Royal Society of Chemistry 2010.