34820-01-4

Upstream product

• 98-88-4 benzoyl chloride 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 92516-59-1 methyl 6-azido-2,3,4-tri-O-benzoyl-6-deoxy-α-D-idopyranoside 
• 124314-27-8 methyl 2,3,6-tri-O-benzoyl-4-O-(trifluoromethylsulfonyl)-β-D-galactopyranoside 
• 52049-72-6 methyl 2,3,6-tri-O-benzoyl-β-D-glucopyranoside 
• 51996-18-0 C₆H₇O(OCOC₆H₅)3(OSO₂CF₃)(OCH₃) 
• 356060-83-8 methyl 2,3,4-tri-O-benzoyl-6-triisopropylsilyl-β-D-galactopyranoside 
• 117124-69-3 methyl 2,3-di-O-benzoyl-β-D-galactopyranoside 

Downstream Products

• 90124-32-6 2,4,6-tri-O-benzyl-3-O-methyl-D-galactopyranose 
• 96120-70-6 methyl 2,3,6-tri-O-benzoyl-4-O-(2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 96103-02-5 methyl 2,3-di-O-benzoyl-4-O-(2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-galactopyranosyl)-β-D-fucopyranoside 
• 96103-33-2 methyl 2,3,6-tri-O-benzoyl-4-O-(4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 96102-99-7 methyl 2,3-di-O-benzoyl-4-O-(4,6-O-benzylidene-α-D-galactopyranosyl)-6-deoxy-6-iodo-β-D-galactopyranoside 
• 96102-98-6 methyl 2,3-di-O-benzoyl-4-O-(4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 96103-31-0 methyl 2,3,6-tri-O-benzoyl-4-O-α-D-galactopyranosyl-β-D-galactopyranoside 
• 96103-00-3 methyl 2,3-di-O-benzoyl-4-O-(4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-fucopyranoside 
• 122204-53-9 methyl 4-O-(2,4,6-tri-O-benzyl-3-O-methyl-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 51996-24-8 methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-β-D-galactopyranoside 
• 51996-25-9 methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-β-D-glucopyranoside 
• 51385-57-0 methyl 4-deoxy-β-D-xylo-hexopyranoside 
• 114682-59-6 methyl O-(2,3,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1-4)-2,3,6-tri-O-benzoyl-β-D-galactopyranoside 
• 191486-09-6 methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-thiocyanato-β-D-glucopyranoside 

Relevant academic research and scientific papers

Quantifying the electronic effects of carbohydrate hydroxy groups by using aminosugar models

Methyl amino-deoxy-glycosides with α- and β-gluco, α-galacto, or α-manno stereochemistry with the amino functionality in each of the four possible non-anomeric positions have been synthesized and their pKa values determined by titration. These

Stereospecific ester activation in nitrite-mediated carbohydrate epimerization

The Lattrell-Dax method of nitrite-mediated substitution of carbohydrate triflates is an efficient method to generate structures of inverse configuration. In the present study, epimerization of gluco- and galactopyranoside derivatives to the corresponding

Elucidation of the mechanism of polysaccharide cleavage by chondroitin AC lyase from Flavobacterium heparinum

Chondroitin AC lyase from Flavobacterium heparinum degrades chondroitin sulfate glycosaminoglycans via an elimination mechanism resulting in disaccharides or oligosaccharides with Δ4,5-unsaturated uronic acid residues at their nonreducing end. Mechanistic details concerning the ordering of the bond-breaking and -forming steps of this enzymatic reaction are nonexistent, mainly due to the inhomogeneous nature of the polymeric substrates. The creation of a new class of synthetic substrates for this enzyme has allowed the measurement of defined and reproducible kcat and Km values and has expanded the range of mechanistic studies that can be performed. The primary deuterium kinetic isotope effect upon kcat/Km for the abstraction of the proton α to the carboxylic acid was measured to be 1.67 ± 0.07, showing that deprotonation occurs in a rate-limiting step. Using substrates with leaving groups of differing reactivity, a flat linear free energy relationship was produced, indicating that the C4-O4 bond is not broken in a rate-determining step. Taken together, these results strongly suggest a stepwise mechanism. Consistent with this was the measurement of a secondary deuterium kinetic isotope effect upon kcat/Km of 1.01 ± 0.03 on a 4-{2H}-substrate, indicating that no sp2 character is developed at C4 during the rate-limiting step, thereby ruling out a concerted syn-elimination.

A mild and efficient approach for the regioselective silyl-mediated protection-deprotection of C-4 hydroxyl group on carbohydrates

A regioselective route is reported, which makes the free 4-OH group of hexopyranoses and derivatives easily and rapidly available. This protocol shows high efficiency on intermediates, such as 1a, which contain a TIPS protective group at C-6 and necessarily a benzoyl group at C-4. Treatment of 1a with TBAF cleaves the TIPS protecting group and gives rise to an intramolecular migration of the benzoyl group at C-4 to the less crowded C-6 position.

Polymer-bound p-alkoxybenzyl trichloracetimidates: Reagents for the protection of alcohols as benzyl ethers on solid-phase

Wang and Tentagel resins ware converted into their trichloroacetimidate dervatives and used as polymer-bound benzylating reagents for a variety of alcohols. Loading and cleavage proceed in good to excellent yields in the presence of BF3.OEt2 and 1% TFA respectively. The resins have excellent shelf life.

Dioxolanylium Ions Derived from Carbohydrates. IX. Rearrangement between Dioxolanylium and Dioxanylium Ions

The formation of 4,6-acetoxonium and benzoxonium ion derivatives of methyl gluco-, manno-, galacto- and idopyranosides from the 6-azido-6-deoxy compounds on treatment with nitrosonium ion is described and the formation and rearrangement of the 3,5-benzoxonium ion derived from methyl α-d-xylofuranoside discussed.

REGIOSELECTIVE STANNYLATION. ACYLATION OF CARBOHYDRATES: COORDINATION CONTROL

An efficient method for the regioselective enhancement of the nucleophilicity of polyhydroxy compounds has been developed.Partial stannylation of carbohydrate with (Bu3Sn)2O and subsequent electrophilic attack with benzoyl chloride gave rise to regioselec

Dioxolanylium Ions Derived from Carbohydrates. VI. Rearrangement of Derivatives of α- and β-Galactopyranosides and Their Reaction with Nucleophiles

The position of the equilibrium 2->/-3 for a number of 2-phenyl-1,3-dioxolanylium ions, fused to carbohydrates of the galacto and gulo configuration, has been measured in acetonitrile solution.THe anomeric configuration was found to influence both the position of the equilibrium between the benzoxonium ions and the outcome of the trans-opening of the benzoxonium ions with bromine ion.