108739-91-9

Upstream product

• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 2397-26-4 N,N-dimethyl(chlorophenylmethylene)ammonium chloride 
• 67-56-1 methanol 
• 38078-09-0 diethylamino-sulfur trifluoride 
• 33535-04-5 methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 194149-26-3 methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 620-05-3 iodomethylbenzene 
• 3162-96-7 methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 
• 73395-15-0 methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 216758-63-3 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-α-D-mannopyranoside 
• 106499-04-1 methyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 73395-14-9 methyl (R,R)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 709-50-2 methyl beta-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 58341-56-3 Methyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 192636-99-0 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-(3-2H)allopyranoside 
• 192637-07-3 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-(2-2H)allopyranoside 
• 192637-01-7 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-triflyl-α-D-(3-2H)allopyranoside 
• 192637-09-5 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-triflyl-α-D-(2-2H)allopyranoside 
• 192637-03-9 [2-2H] 2-O-benzyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose 
• 109010-30-2 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose 
• 29741-67-1 1,3,4,6-tetra-O-acetyl-2-O-benzyl-β-D-glucopyranoside 
• 30253-76-0 1,3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranoside 
• 129948-13-6 methyl 3-O-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 129948-12-5 methyl 3-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 148312-79-2 methyl 3-O-acetyl-2-O-benzyl-β-D-glucopyranoside 
• 15038-69-4 methyl β-D-glucopyranoside 2-benzyl ether 
• 114284-11-6 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 

Relevant academic research and scientific papers

Modified bleomycin disaccharides exhibiting improved tumor cell targeting

The bleomycins (BLMs) are a family of antitumor antibiotics used clinically for anticancer chemotherapy. Their antitumor selectivity derives at least in part from their ability to target tumor cells, a property that resides in the carbohydrate moiety of the antitumor agent. In earlier studies, we have demonstrated that the tumor cell selectivity resides in the mannose carbamoyl moiety of the BLM saccharide and that both the BLM disaccharide and monosaccharide containing the carbamoyl moiety were capable of the delivery/uptake of a conjugated cyanine dye into cultured cancer cell lines. Presently, the nature of the participation of the carbamoyl moiety has been explored further to provide compounds of utility for defining the nature of the mechanism of tumor cell recognition and uptake by BLM saccharides and in the hope that more efficient compounds could be identified. A library of seven disaccharide-Cy5 dye conjugates was prepared that are structural analogues of the BLM disaccharide. These differed from the natural BLM disaccharide in the position, orientation, and substitution of the carbamoyl group. Studies of these compounds in four matched sets of tumor and normal cell lines revealed a few that were both tumor cell selective and internalized 2-4-fold more efficiently than the natural BLM disaccharide.

p-Methoxybenzyl ether cleavage by polymer-supported sulfonamides.

[reaction: see text] p-Methoxybenzyl ethers have been found to transfer from alcohols to sulfonamides in the presence of catalytic trifluoromethanesulfonic acid. This process for protecting group removal can be performed in solution with yields >94%. Through the use of sulfonamide-functionalized ("safety-catch") resins, p-methoxybenzyl ethers can be cleaved in excellent yields with minimal purification.

Improvements in the regioselectivity of alkylation reactions of stannylene acetals

The regioselectivity of benzylation of stannylene acetals of trans-diols on pyranose rings is improved by performing the reaction in benzyl bromide, for instance, for methyl 4,6-O-benzylidene-2,3-O-dibutylstannylene-α-D-glucopyranoside, the ratio of 2-O-b

Organotin-catalyzed regioselective benzylation of carbohydrate trans-diols

A convenient approach to regioselective benzylation of carbohydrate trans-diols was developed, where 0.1 equiv. of Bu2SnCl2 and 0.1 equiv. of TBABr were used as the catalysts and 2.0 equiv. of BnCl was used as the benzylation reagent. In most cases, similar or better benzylation regioselectivities and isolated yields were obtained by using catalytic amounts of Bu2SnCl2, rather than stoichiometric amounts of organotin reagents required.

Synthesis and binding affinity analysis of α1-2- and α1-6-O/S-linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors

The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards α1-2- and α1-6-linked dimannosides with S- or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrene-mediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the α1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the α1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the α1-2-analog displayed very similar binding compared to the O-linked structure.

Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside

We discovered that the cobalt-propargyl cation can mediate the glycosylation reaction by activating the thioglycoside donor. The glyco-oxacarbenium cation was formed by transferring the thio-aglycone to the cobalt-propargyl cation that was generated from the cobalt-propargylated acceptor in situ via the activating with Lewis acid. The reactivity of the donor (Armed or dis-armed) and the amount of the Lewis acid control the releasing rate of the cobalt-propargyl group.

Regioselective alkylation of carbohydrates and diols: A cheaper iron catalyst, new applications and mechanism

As an extension of our previous research on the regioselective protection of carbohydrates and diols, we developed an iron catalyst, Fe(dibm)3 (dibm = diisobutyrylmethane), which has an unusually broad catalytic scope in the selective monoalkyl

Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine

We report a synthetic glycosylation reaction between sucrosyl acceptors and glycosyl fluoride donors to yield the derived trisaccharides. This reaction proceeds at room temperature in an aqueous solvent mixture. Calcium salts and a tertiary amine base promote the reaction with high site-selectivity for either the 3′-position or 1′-position of the fructofuranoside unit. Because nonenzymatic aqueous oligosaccharide syntheses are underdeveloped, mechanistic studies were carried out in order to identify the origin of the selectivity, which we hypothesized was related to the structure of the hydroxyl group array in sucrose. The solution conformation of various monodeoxysucrose analogs revealed the co-operative nature of the hydroxyl groups in mediating both this aqueous glycosyl bond-forming reaction and the site-selectivity at the same time.

Acceptor Reactivity in the Total Synthesis of Alginate Fragments Containing α- L -Guluronic Acid and β- D -Mannuronic Acid

The total synthesis of mixed-sequence alginate oligosaccharides, featuring both β-D-mannuronic acid (M) and α-L-guluronic acid (G), is reported for the first time. A set of GM, GMG, GMGM, GMGMG, GMGMGM, GMGMGMG, and GMGGMG alginates was assembled using GM

Regioselective benzylation of diols and polyols by catalytic amounts of an organotin reagent

An efficient one-pot method for the selective benzylation of diols and polyols using 0.1 equiv. of organotin reagents and tetrabutylammonium bromide as catalyst has been developed. The diols and polyols containing a cis-vicinal diol were regioselectively