58006-32-9

Usage

Chemical Properties

White Solid

Upstream product

• 4304-12-5 (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 34246-23-6 benzyl D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 100-52-7 benzaldehyde 
• 83049-98-3 2,4,6-tri-O-acetyl-3-O-tosyl-β-D-glucopyranosyl bromide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 10343-13-2 benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 83049-99-4 benzyl 2,4,6-tri-O-acetyl-3-O-tosyl-β-D-glucopyranoside 
• 83050-00-4 benzyl 2-O-acetyl-4,6-O-benzylidene-3-O-tosyl-β-D-glucopyranoside 
• 100-51-6 benzyl alcohol 
• 2280-44-6 D-Glucose 
• 25320-99-4 benzyl α-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 83-87-4 D-glucose pentaacetate 

Downstream Products

• 22893-77-2 benzyl-[O²,O³-diacetyl-O⁴,O⁶-((R)-benzylidene)-β-D-glucopyranoside] 
• 70144-60-4 benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 86420-81-7 benzyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 183953-29-9 benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 67831-41-8 benzyl 2,3-di-O-benzyl-β-D-glucopyranoside 
• 154774-22-8 benzyl 4,6-O-benzylidene-2,3-O-bis(3,4,5-tris(benzyloxy)benzoyl)-β-D-glucopyranoside 
• 67831-42-9 benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 64656-66-2 Benzyl-2,3-di-O-acetyl-4,6-di-O-benzyl-β-D-glucopyranosid 
• 57783-66-1 benzyl 4,6-O-benzylidene-2,3-tri-O-benzyl-β-D-glucopyranoside 
• 64656-65-1 Benzyl-2,3-di-O-acetyl-β-D-glucopyranosid 
• 87591-38-6 Benzyl-2,3-di-O-acetyl-4-O-benzyl-β-D-glucopyranosid 
• 127138-46-9 benzyl 6-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 127138-45-8 benzyl 4-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 127138-48-1 (2S,3R,4S,5R)-2-((2R,3R,4S,5R,6R)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3,4,5-triol 

Relevant academic research and scientific papers

INHIBITORS OF MALARIAL AND PLASMODIUM FALCIPARUM HEXOSE TRANSPORTER AND USES THEREOF

Provided are molecules capable of binding to binding pockets of Plasmodium falciparum hexose transporter (PfHT) or analogs thereof and complexes comprising the same. Also provided herein are inhibitors of PfHT, pharmaceutical compositions comprising the i

Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates

Boron neutron capture therapy (BNCT) is a noninvasive binary therapeutic modality applicable to the treatment of cancers. While BNCT offers a tumor-targeting selectivity that is difficult to match by other means, the last obstacles preventing the full har

Synthesis of Bradyrhizose from d -Glucose

We describe the synthesis of the unusual bicyclic sugar bradyrhizose in 14 steps and a 6% overall yield from d-glucose. The synthesis involves the elaboration of a trans-fused carbocyclic ring onto the preexisting glucopyranose framework followed by adjus

Synthesis of the trisaccharide repeating unit of capsular polysaccharide from Klebsiella pneumoniae

The incidences of primary, pyrogenic liver abscess complicated by meningitis and septic endophthalmitis caused by Klebsiella pneumoniae has increased globally. Earlier studies have shown that the capsular polysaccharide (CPS) of Klebsiella pneumoniae plays an important role in the resistance to phagocytosis and related pathogenicity. The first chemical synthesis of the trisaccharide repeating unit of this CPS has been achieved via stereoselective glycosylation with orthogonal and appropriate protecting groups. A new method for the pyruvylation of trans diol was developed.

Chemical Approach to Positional Isomers of Glucose-Platinum Conjugates Reveals Specific Cancer Targeting through Glucose-Transporter-Mediated Uptake in Vitro and in Vivo

Glycoconjugation is a promising strategy for specific targeting of cancer. In this study, we investigated the effect of d-glucose substitution position on the biological activity of glucose-platinum conjugates (Glc-Pts). We synthesized and characterized all possible positional isomers (C1α, C1β, C2, C3, C4, and C6) of a Glc-Pt. The synthetic routes presented here could, in principle, be extended to prepare glucose conjugates with different active ingredients, other than platinum. The biological activities of the compounds were evaluated both in vitro and in vivo. We discovered that varying the position of substitution of d-glucose alters not only the cellular uptake and cytotoxicity profile but also the GLUT1 specificity of resulting glycoconjugates, where GLUT1 is glucose transporter 1. The C1α- and C2-substituted Glc-Pts (1α and 2) accumulate in cancer cells most efficiently compared to the others, whereas the C3-Glc-Pt (3) is taken up least efficiently. Compounds 1α and 2 are more potent compared to 3 in DU145 cells. The α- and β-anomers of the C1-Glc-Pt also differ significantly in their cellular uptake and activity profiles. No significant differences in uptake of the Glc-Pts were observed in non-cancerous RWPE2 cells. The GLUT1 specificity of the Glc-Pts was evaluated by determining the cellular uptake in the absence and in the presence of the GLUT1 inhibitor cytochalasin B, and by comparing their anticancer activity in DU145 cells and a GLUT1 knockdown cell line. The results reveal that C2-substituted Glc-Pt 2 has the highest GLUT1-specific internalization, which also reflects the best cancer-targeting ability. In a syngeneic breast cancer mouse model overexpressing GLUT1, compound 2 showed antitumor efficacy and selective uptake in tumors with no observable toxicity. This study thus reveals the synthesis of all positional isomers of d-glucose substitution for platinum warheads with detailed glycotargeting characterization in cancer.

TANNIN INHIBITORS OF HIV

The invention provides a method to prevent or treat HIV-infection with synthetic tannins, and pharmaceutical compositions comprising synthetic tannins.

Synthesis and biological profiling of tellimagrandin I and analogues reveals that the medium ring can significantly modulate biological activity

A novel synthesis of the ellagitannin natural product tellimagrandin I and a series of medium ring analogues is described. These compounds were all subsequently screened for redox activity, ability to precipitate protein and cellular phenotype in HeLa cel

First and biomimetic total synthesis of a member of the C-glucosidic subclass of ellagitannins, 5-O-desgalloylepipunicacortein A

The first total synthesis of a member of the C-glucosidic subclass of ellagitannins, 5-O-desgalloylepipunicacortein A, was accomplished by relying on a biomimetic aldol-type formation of its characteristic C-aryl glucosidic bond through the exploitation of the inherent chemical reactivity of a glucopyranosic hemiacetal precursor.

An efficient method for the synthesis of a 1,6-anhydro-α-D-galactofuranose derivative and its application in the synthesis of oligosaccharides

Synthesis of 1,6-anhydro-2,3,5-tri-O-benzoyl-β-D-galactofuranose (3) has been achieved in good yield by stannic chloride catalysed ring closure of methyl 2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactofuranoside (1). The anhydro compound 3 was converted to the

Dehydrative glycosylation by diethylaminosulfur trifluoride (DAST) - tin(II) trifluoromethanesulfonate-tetrabutylammonium perchlorate - triethylamine system

Dehydrative glycosylation using 2,3,4,6-tetra-O-benzyl-D-glucopyranose was carried out by the use of a condensing reagent system composed of diethylaminosulfur trifluoride (DAST), tin(II) triflate, tetrabutylammonium perchlorate, and triethylamine. Using this system, two tetrasaccharides, O- a-D-glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→3)-Oα-D-glucopyranosyl- (1→4)-D-glucopyranose and O-a-D-glucopyranosyl-(1→3)-O-α-D- glucopyranosyl-(1→4)-O-α-D-glucopyranosyl-(1→4)-D-glucopyranose, were synthesized.