38184-15-5

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 88567-49-1 6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose 
• 787623-80-7 p-methylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside 
• 4356-77-8 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose 
• 35094-58-7 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl bromide 
• 479252-05-6 ((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol 

Downstream Products

• 145149-86-6 O-(6-O-Acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-1-O-acetyl-2,3,4-tri-O-benzyl-α,β-D-glucopyranose 
• 116730-82-6 Methyl O-(2,3,4-tri-O-benzyl-6-deoxy-6-fluoro-β-D-glucopyranosyl)-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 116730-79-1 Methyl O-(2,3,4-tri-O-benzyl-6-deoxy-6-fluoro-α-D-glucopyranosyl)-(1-6)-tri-O-benzyl-α-D-glucopyranoside 
• 116730-84-8 Methyl O-(2,3,4-tri-O-benzyl-6-deoxy-6-fluoro-α-D-glucopyranosyl)-(1-6)-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 116730-86-0 Methyl O-(2,3,4-tri-O-benzyl-6-deoxy-6-fluoro-β-D-glucopyranosyl)-(1-6)-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1-6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 110383-80-7 Trimethyl-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-silane 
• 53810-61-0 methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

A "traceless" Directing Group Enables Catalytic SN2 Glycosylation toward 1,2- cis-Glycopyranosides

Generally applicable and stereoselective formation of 1,2-cis-glycopyranosidic linkage remains a long sought after yet unmet goal in carbohydrate chemistry. This work advances a strategy to this challenge via stereoinversion at the anomeric position of 1,2-trans glycosyl ester donors. This SN2 glycosylation is enabled under gold catalysis by an oxazole-based directing group optimally tethered to a leaving group and achieved under mild catalytic conditions, in mostly excellent yields, and with good to outstanding selectivities. The strategy is also applied to the synthesis of oligosaccharides.

HEPARANASE INHIBITORS FOR TREATMENT OF DIABETES

Anti-heparanase compounds for the treatment of diabetes are described. The anti-heparanase compounds are high affinity, synthetic glycopolymers that result in minimal anticoagulant activity. Stereoselective fluorinated forms of these compounds are also pr

HEPARANASE INHIBITORS AND THEIR USE AS ANTI-CANCER COMPOUNDS

Anti-heparanase compounds for the treatment of cancer are described. The anti-heparanase compounds are high affinity, synthetic glycopolymers that result in minimal anticoagulant activity. Stereoselective fluorinated forms of these compounds are also prov

Phenanthroline-Catalyzed Stereoretentive Glycosylations

Carbohydrates are essential moieties of many bioactive molecules in nature. However, efforts to elucidate their modes of action are often impeded by limitations in synthetic access to well-defined oligosaccharides. Most of the current methods rely on the

A flexible 1,2-cis α-glycosylation strategy based on in situ adduct transformation

A flexible 1,2-cis α-selective glycosylation strategy for a wide range of glycosyl donors and acceptors has been developed, which is based on an in situ adduct transformation protocol. Based on this strategy, both NFM-derived and iodide covalent adducts c

Conformational effects on glycoside reactivity: Study of the high reactive conformer of glucose

The effect of conformation on glycoside reactivity was investigated by studying the hydrolysis of a selection of 3,6-anhydroglucosides as models for glucose in the highly reactive 1C4 conformation. Methyl 3,6-anhydro-β-D-glucopyranoside was found to hydrolyze 200-400 times faster than methyl glucosides in the 4C1 conformation, while methyl 3,6-anhydro-β-D-galactopyranoside, which is in the B1,4 conformation, was less reactive than methyl β-D-galactopyranoside. Methyl (3,6-anhydro-β-D-glucopyranosyl)-(1 → 6)-α-D-glucopyranoside, methyl (3,6-anhydro-α-D-glucopyranosyl)-(1 → 6)-α-D- glucopyranosyl-(1 → 6)-α-D-glucopyranoside, and methyl (3,6-anhydro-β-D-glucopyranosyl)-(1 → 6)-α-D-glucopyranosyl-(1 → 6)-α-D-glucopyranoside were prepared and found to react selectively at the anhydro residue. The finding that 1C4 conformers of glucosides are highly reactive species is in accordance with and supports previous results showing that axial OH groups are less electron withdrawing than equatorial OH groups.

SYNTHESIS OF METHYL 6"-DEOXY-6'-FLUORO-α-ISOMALTOSIDE AND OF THE CORRESPONDING TRISACCHARIDE

Methyl 6-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (5) was formed with high stereoselectivity when the condensation of methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyl (1) with 6-O-acetyl-2,3,4-tri-O-benzyl-α-

α-D-glucosylation by 6-O-Acetyl-2,3,4-tri-O-benzyl-D-glucopyranose Using Trimethylsilyl Triflate and Pyridine. Synthesis of α-Maltosyl and α-isomaltosyl α-D-Glucosides

The D-glucosylation of methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside and methyl 2,3,6-tri-O-benzyl-β-D-glucupyranoside by 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose using pyridine and excess trimethylsilyl triflate was carried out in dichloromethane, 1,2 dimethoxyethane, and acetonitrile.In a given solvent, the selectivity of the reaction varied depending on the type of hydroxyl group of the glucosyl acceptors.The D-glucosylation of these acceptors with 6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose employing this reagent system in dichloromethane proceeded with good α-selectivity irrespective of the type of the hydroxyl group.This α-D-glucosylation was applied for the synthesis of O-α-D-glucopyranosyl-(1->4)- and -(1->6)-α-D-glucopyranosyl α-D-glucopyranosides from α,α-trehalose.