90465-39-7

Upstream product

• 55659-53-5 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide 
• 100-51-6 benzyl alcohol 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 51532-75-3 3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 
• 108869-64-3 3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 53929-30-9 benzyl 3,4,6-tetra-O-benzyl-β-G-glucopyranoside 
• 67-56-1 methanol 
• 301645-84-1 phenyl 2-O-(1-benzyloxy-2-iodopropyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 20672-66-6 3,4,6-tri-O-benzyl-D-mannopyranose 
• 100-39-0 benzyl bromide 
• 5194-96-7 N-phthaloyl-L-serine tert-butyl ester 

Downstream Products

• 112289-03-9 benzyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 112302-50-8 benzyl 3,4,6-tri-O-benzyl-2-O-(3,4,6-tri-O-acetyl-2-O-allyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 112289-15-3 benzyl 2-O-(2-O-allyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 112289-17-5 benzyl 2-O-(2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 112289-05-1 benzyl-O-(3,4,6-tri-O-acetyl-2-O-allyl-α-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->2)-3,4-6-tri-O-benzyl-β-D-glucopyranoside 
• 147624-27-9 1-Benzyl-4-benzyloxy-1H-indole-3-carboxylic acid (2R,3R,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 185380-26-1 (2S,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-2,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 262599-35-9 benzyl O-[3,4,6-tri-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranosyl]-(1->2)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 144261-01-8 benzyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 90465-40-0 benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-fluoro-β-D-glucopyranoside 
• 1423019-37-7 benzyl 3,4,6-tri-O-benzyl-β-d-arabino-hexos-2-ulo-pyranoside 

Relevant academic research and scientific papers

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

Simple and mild stereoselective O-glycosidation using 1,2-anhydrosugars under neutral conditions

The ring opening of α-D-1,2-anhydrohexapyranoses with phenols proceeded smoothly in ethyl acetate (neutral conditions) in the absence of metal ion catalysts or additives to stereoselectively furnish 1,2-cis-α-aryl glycosides as the major product and 1,2-t

An Unexpected FeCl 3/C-Catalyzed β-Stereoselective Glycosylation in the Presence of the C(2)-Benzyl Group

An efficient and completely β-stereoselective glycosylation that did not rely on neighboring group participation is described using 2-20 molpercent FeCl 3 /C as the catalyst and benzylated propargyl glycosides as the donors to reach yields up to 96percent under mild condition. With an octatomic-ring intermediate at the α-face of FeCl 3 /C with alkyne of propargyl glycosides, a panel of aglycones comprising aliphatic, alicyclic, unsaturated alcohols, halogenated alcohols, and phenols with different substitution were examined successfully for the exclusive β-stereoselective glycosylation reaction.

Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides

Ionic liquids promoted the direct epoxidation of glycals acting as PTC. 1,2-anhydrosugars were prepared by the oxidation of glycals under biphasic conditions with dimethydioxirane generated in situ from oxone/acetone and amphiphilic IL's as catalysts. β-O

Stereoselective β-mannosylation via anomeric O-alkylation: Formal synthesis of potent calcium signal modulator acremomannolipin A

Stereoselective β-mannosylation has been investigated via cesium carbonate-mediated anomeric O-alkylation of D-mannose-derived lactol with various electrophiles. It was found that electrophiles bearing trifluoromethanesulfonate (triflate) as the leaving g

Glycosyl dithiocarbamates: β-selective couplings without auxiliary groups

In this article, we evaluate glycosyl dithiocarbamates (DTCs) with unprotected C2 hydroxyls as donors in β-linked oligosaccharide synthesis. We report a mild, one-pot conversion of glycals into β-glycosyl DTCs via DMDO oxidation with subsequent ring opening by DTC salts, which can be generated in situ from secondary amines and CS2. Glycosyl DTCs are readily activated with Cu(I) or Cu(II) triflate at low temperatures and are amenable to reiterative synthesis strategies, as demonstrated by the efficient construction of a tri-β-1,6-linked tetrasaccharide. Glycosyl DTC couplings are highly β-selective despite the absence of a preexisting C2 auxiliary group. We provide evidence that the directing effect is mediated by the C2 hydroxyl itself via the putative formation of a cis-fused bicyclic intermediate.

Access to new carbohydrate-functionalized polylactides via organocatalyzed ring-opening polymerization

The 4-dimethylaminopyridine (DMAP) catalyzed ring-opening polymerization of lactide using various carbohydrate initiators has been assessed for the functionalization of polylactide. Selectively protected glucose derivatives bearing a free primary alcohol (Glc-1r) and a free secondary alcohol (Glc-2r), glucose and cyclodextrin diol derivatives (Glc-diol and CD-diol), methyl-α-d-glucopyranoside (Glc-Me) and native β-cyclodextrin (CD) were used as initiators. According to the solubility of the carbohydrate derivative, the polymerizations were conducted in chlorinated solvents and in the bulk. Relatively narrow distributions are obtained in high yields in the absence of side reactions, affording a 100% functionalization efficiency. The catalytic synthesis of new carbohydrate link-functionalized polylactides and carbohydrate core star polylactides is reported.

Regioselective alkylation of carbohydrate derivatives catalyzed by a diarylborinic acid derivative

Regioselective, catalyst-controlled monoalkylations of cis-vicinal diol motifs in carbohydrate derivatives, using a diphenylborinic ester precatalyst, are described. Selective installation of benzyl, naphthylmethyl, 4-bromobenzyl and benzyloxymethyl protective groups at a single secondary hydroxy group of ten representative carbohydrate derivatives illustrates the scope of this method. This new mode of catalytic reactivity represents an operationally simple method to access useful monoalkylated building blocks while avoiding the use of stoichiometric quantities of organotin reagents.

Allyl protecting group mediated intramolecular aglycon delivery: Optimisation of mixed acetal formation and mechanistic investigation

An efficient protocol for the formation of α-iodo mixed acetals, the first step of allyl-mediated IAD, by reaction of allyl-derived enol ethers and alcohols, using I2, AgOTf and di-tert-butyl methylpyridine as a novel source of I+, i

Stereoselective 1,2-cis glycosylation of 2-O-Allyl protected thioglycosides

The technique of intramolecular aglycon delivery (IAD), whereby a glycosyl acceptor is temporarily appended to a hydroxyl group of a glycosyl donor is an attractive method that can allow the synthesis of 1,2-cis glycosides in an entirely stereoselective f