247017-29-4

Upstream product

• 54325-28-9 6-O-trityl-D-glucopyranose 
• 98-88-4 benzoyl chloride 
• 76-83-5 trityl chloride 
• 2280-44-6 D-Glucose 
• 50-99-7 D-glucose 

Downstream Products

• 104707-01-9 1,2,3,4-tetra-O-benzoyl-β-D-glucopyranose 
• 114298-48-5 1,2,3,4-tetra-O-benzoyl-α-D-glucopyranose 
• 257614-50-9 2,3,4-tri-O-benzoyl-6-O-trityl-α-D-glucopyranosyl trichloroacetimidate 
• 1122631-46-2 C₃₇H₃₀O₁₁ 
• 1122631-50-8 C₃₂H₂₆Cl₃NO₁₀ 
• 427-04-3 2,3,4-tri-O-benzoyl-6-O-triphenylmethyl-α-D-glucopyranosyl fluoride 
• 114244-21-2 1,2,3,4-tetra-O-benzoyl-6-O-chloroacetyl-α-D-glucopyranose 
• 590367-95-6 1,2,3,4-tetra-O-benzoyl-D-glucopyranoside 
• 114244-15-4 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-glucopyranosyl bromide 
• 114244-22-3 1,2,3,4-tetra-O-benzoyl-6-O-chloroacetyl-β-D-glucopyranose 

Relevant academic research and scientific papers

Synthesis of α-O- and α-S-glycosphingolipids related to sphingomonous cell wall antigens using anomerisation

Analogues of glycolipids from Spingomonadacaece with O- and S- and SO 2-linkages have been prepared using chelation induced anomerisation promoted by TiCl4. Included are examples of the anomerisation of intermediates with O- and S-glycosidic linkages as well as isomerisation of β-thioglycuronic acids (β-glycosyl thiols). The β-O-glucuronide and β-O-galacturonide precursors were efficiently prepared using benzoylated trichloroacetimidates. β-Glycosyl thiols were precursors to β-S-derivatives. Triazole containing mimics of the natural glycolipids were prepared using CuI promoted azide-alkyne cycloaddition reactions in THF. The glycolipid antigens are being evaluated currently for their effects on iNKT cells.

α-glycosphingolipids via chelation-induced anomerization of O- And s-glucuronic and galacturonic acid derivatives

Bacterial glycolipids containing either α-glucuronic acid or α-galacturonic acid residues have an important role in the innate-type immune response to Gram-negative bacteria. Synthesis of closely related compounds, including a novel α-SO2 glycolipid mimetic, is described from carbohydrate precursors where anomerization is a key step. Very high stereoselectivites (>97:3 in favor of α) were observed from O-glycoside precursors.

SYNTHESES OF A BRANCHED HEPTASACCHARIDE HAVING PHYTOALEXIN-ELICITOR ACTIVITY

Synteses are described of a D-glucose heptasaccharide, 1, corresponding to a glucan structure recognised by the soybean when infected by the fungus Phytophtora megasperma f. sp. glycinea and which stimulates the formation of phytoalexins.The synthetic strategy is based upon 1,2-trans-glycoside formation assisted by participating benzoate groups in the 2-position, with silver triflate as promoter and glycosyl bromides as donors for making the smaller fragments, and with methyl triflate as promoter with thioglycosides as donors for making the larger ones.Regioselective reductive openings of 4,6 benzylidene acetals play a key role in obtaining free 6-OH groups with benzyl protection at O-4.