136882-36-5

Upstream product

• 79528-49-7 phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 108-98-5 thiophenol 
• 31505-45-0 2-deoxy-2-phthalimido-β-D-glucopyranose 
• 14131-63-6 D-glucosamine hydrochloride 
• 85-44-9 phthalic anhydride 
• 17314-33-9 tributyltin phenyl sulfide 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 72858-55-0 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 31505-45-0 2-deoxy-2-phthalimido-D-glucopyranose 

Downstream Products

• 177421-30-6 2-((4aR,6S,7R,8R,8aS)-8-Hydroxy-2,2-dimethyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione 
• 141342-83-8 phenyl 6-O-benzyl-2-deoxy-2-phthalimido-1-thio-1-deoxy-β-D-glucopyranoside 
• 196697-91-3 phenyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 176106-81-3 Galβ1-4(Fucα1-3)GlcNAcβ1-OMe 
• 492440-46-7 phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 492440-45-6 phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-4,5-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 492440-47-8 phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-6-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 492440-52-5 methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 492440-48-9 phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-6-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 492440-49-0 11-bromo-undecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 492440-53-6 11-acetylsulfanyl-undecyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 159734-70-0 phenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 159734-71-1 phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 208644-74-0 methyl 2,3-di-O-benzoyl-4,6-O-((R)-1-methoxycarbonylethylidene)-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3) 2,4-di-O-benzyl-β-L-fucopyranoside 

Relevant academic research and scientific papers

P- tert-Butyl Groups Improve the Utility of Aromatic Protecting Groups in Carbohydrate Synthesis

Aromatic protective groups are widely used in carbohydrate synthesis owing to their numerous merits. However, they unpredictably make certain compounds insoluble in organic solvents owing to their π-stacking abilities. It was found that introducing a tert

IMMUNOGENIC COMPOSITIONS

The present invention is directed towards conjugates comprising fragments of the capsular polysaccharide of Type III Group B Streptococcus (GBS). Suitable fragments may be produced synthetically or by depolymerisation of native polysaccharide.

Design, synthesis and evaluation of cytotoxic properties of bisamino glucosylated antitumor ether lipids against cancer cells and cancer stem cells

Glycosylated antitumor ether lipids (GAELs) are a class of amphiphilic antitumor agents that kill cancer cells by a non-apoptotic pathway. Previous studies have shown that 2-amino-2-deoxy-d-gluco-based GAELs such as α-GLN and β-GLN show greatly improved antitumor activity against epithelial cancer cells and stem cells. To further optimize the bioactivity, we prepared a series of diamino-d-gluco-based GAELs and their analogs, and screened them against a panel of human epithelial cancer cell lines and cancer stem cells. Most of the new GAEL analogs are more potent than chlorambucil, cisplatin and salinomycin. The most potent bisamine-based GAEL analogs 1, 2, 4 and 8 showed 2- to 3-fold enhanced cytotoxicity against various cancer cell lines when compared to β-GLN, indicating that the addition of a second amino group enhances the cytotoxic effect. The effect of the most active dicationic GAELs 1 and 4 on cancer stem cells isolated from breast (BT-474) and prostate (DU-145) cell lines revealed that the two GAELs inhibited the formation of tumor spheres and resulted in >95% loss of viability of the cancer stem cells at 5 μM. Activity of GAEL 1 against BT-474 cancer stem cells is superior to that of salinomycin.

DI- AND TRI-CATIONIC GLYCOSYLATED ANTITUMOR ETHER LIPIDS, L-GUCOSYLATED GAELS AND RHAMNOSE-LINKED GAELS AS CYTOTOXIC AGENTS AGAINST EPITHELIAL CANCER CELLS AND CANCER STEM CELLS

Glycosylated Antitumor Ether Lipids (GAELs) kill cancer cells by a nonapoptotic pathway which is an attractive strategy to avoid resistance. To further optimize the antitumor effect, we prepared various analogs of di-, and tri-cationic GAEL analogs differing in the nature of the sugar (D-giucose or L-glucose), the anomeric linkage as well as position of the glycerolipid moiety. The di- and tri-cationic GAELs were synthesized and their in vitro anticancer properties were evaluated against drug resistant and aggressively growing cancer cell lines derived from human breast, prostate, pancreatic and ovarian cancers. The most potent dicationic GAEL analogs were also studied against cancer stem cells obtained from breast BT 474, prostate DU145 and ovarian A2780cp cell lines. Our results indicate that the number of positive charges, the position of the amino substituents and the nature of the sugar have significant effects on the anticancer activities of these compounds. The most active analog kill 50% of the cells at concentration range of 0.5-5μΜ and 90% of the cells at the concentration of 1-10μΜ depending on type of cancer cells.

Random-coil:α-helix equilibria as a reporter for the Lewis X-LewisX interaction

Probing weak interactions: A peptide random-coil:α-helix equilibrium has been used to identify a weak carbohydrate-carbohydrate interaction (CCI). Glucose and lactose destabilized the helical conformer while LewisX trisaccharide led to increased helicity. Though small, the trend observed indicates that this peptide reporter can detect a single CCI in isolation. Copyright

Concise syntheses of bacteriohopanetetrol and its glucosamine derivative

This study describes the syntheses of bacteriohopanetetrol and its glucosamine derivative through a key direct coupling of a ribose derivative to the hopane skeleton. The Royal Society of Chemistry 2005.

Synthesis of Lex-neoglycoconjugate to study carbohydrate-carbohydrate associations and its intramolecular interaction

A straightforward synthetic strategy for the preparation of the Lex neoglycoconjugate (11,11′-dithio bis[undecanyl-β-D-galactopyranosyl-(1→4)-α-L-fucopyranosyl- (1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside]) and methyl Lex glycoside

Optimized synthesis of an orthogonally protected glucosamine

Glucosamine hydrochloride was transformed into an orthogonally protected intermediate in seven steps and 34% overall yield. The synthesis includes an optimized preparation of N-phthaloyl-β-D-glucosamine tetraacetate, a commonly used precursor in carbohydrate chemistry.

Chemical synthesis of (4,6-Pyr)-Gal β1→4GlcNacβ1→3Fucβ1→OMe: A pyruvated trisaccharide related to the cell aggregation of the sponge Microciona prolifera

4,6-O-[(R)-1-carboxylethylidene] Galβ1→4GlcNAcβ1→3Fucβ1→OMe, a pyruvated trisaccharide unit involved in the aggregation factor of the marine sponge Microciona prolifera, was synthesized stereospecifically and unambiguously employing thioglycosides as glycosyl donors to construct glycosidic bonds.

Synthesis of mono-, di- and trisulfated Lewis x trisaccharides

3'-Sulfated and 3',6-disulfated Lewis x trisaccharides have been prepared through selective sulfation of methyl 2-acetamido-6-O-benzyl-2- deoxy-4-O-β-D-galactopyranosyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)- β-Dglucopyranoside, followed by catalytic