15038-69-4

Upstream product

• 141115-75-5 methyl 2-O-benzyl-4,6-di-O-benzylidene-α-D-altropyranoside 
• 7664-93-9 sulfuric acid 
• 67-64-1 acetone 
• 67-56-1 methanol 
• 50711-01-8 1,6-anhydro-2-O-benzyl-β-D-glucopyranose 
• 15038-71-8 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 76375-66-1 methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 81348-26-7 methyl 2-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranoside 
• 108-86-1 bromobenzene 
• 3646-73-9 α-D-galactopyranose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 824-94-2 p-methoxybenzyl chloride 
• 130192-76-6 methyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 4860-85-9 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 

Downstream Products

• 55735-75-6 methyl 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranoside 
• 78142-18-4 (2R,3S,4S,5R,6S)-5-Benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3,4-diol 
• 332057-67-7 Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 
• 332057-71-3 [(1R,3S,4R,4aS,17aR)-4-Benzyloxy-3-methoxy-11-(toluene-4-sulfonyl)-dodecahydro-2,5,8,14,17-pentaoxa-11-aza-benzocyclopentadecen-1-yl]-methanol 
• 332057-88-2 (1R,3S,4R,4aS,17aR)-4-Benzyloxy-1-butoxymethyl-3-methoxy-11-(toluene-4-sulfonyl)-dodecahydro-2,5,8,14,17-pentaoxa-11-aza-benzocyclopentadecene 
• 332057-69-9 (2S,3R,4S,5R,6R)-3-Benzyloxy-4,5-bis-[2-(2-chloro-ethoxy)-ethoxy]-2-methoxy-6-trityloxymethyl-tetrahydro-pyran 
• 332057-86-0 (1R,3S,4R,4aS,17aR)-4-Benzyloxy-3-methoxy-11-(toluene-4-sulfonyl)-1-trityloxymethyl-dodecahydro-2,5,8,14,17-pentaoxa-11-aza-benzocyclopentadecene 
• 58769-74-7 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranose 
• 100759-92-0 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranose 
• 72984-63-5 1,3,4,6-tetra-O-acetyl-2-O-benzyl-α- and β-D-glucopyranose 
• 1198465-10-9 methyl 2-O-benzyl-3,4,6-tri-O-methyl-α-D-glucopyranoside 
• 1379442-45-1 methyl 2-O-benzyl-4-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside 
• 1379442-48-4 methyl 2-O-benzyl-6-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside 
• 99152-61-1 methyl 3-O-acetyl-2-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols

In this study, [Fe(dibm)3] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1,2- and 1,3-diol-containing structures. The mechanism is proposed to proceed via a cyclic dioxolane-type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition-metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation.

Polyvalent effect enhances diglycosidic antiplasmodial activity

An efficient and facile total synthesis of diglycoside Matayoside D isolated from the root bark of Matayba guianensis with antiplasmodial activity have been accomplished in 11 steps with 5% overall yields starting from commercially available glucose and rhamnose. Furthermore, a class of the diglycosidic derivatives with different lengths of the linker and valences were also prepared and evaluated for their antiplasmodial activities against chloroquine-susceptible (3D7) and chloroquine-resistant (W2) strains of Plasmodium falciparum. Low valent and short linker attached diglycoside show no enhancement of the antiplasmodial activity while polyvalent conjugates showed enhanced antiplasmodial activity with IC50 value at least 20 fold better than that of the corresponding diglycosidic monomer. The polyvalent diglycoside were non-cytotoxic against normal mammalian cells under 50,000 μg/L.

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.

The synthesis and antitumor activity of twelve galloyl glucosides

Twelve galloyl glucosides 1-12, showing diverse substitution patterns with two or three galloyl groups, were synthesized using commercially available, low-cost D-glucose and gallic acid as starting materials. Among them, three compounds, methyl 3,6-di-O-galloyl-?±-D-glucopyranoside (9), ethyl 2,3-di-O-galloyl-?±-D-glucopyranoside (11) and ethyl 2,3-di-O-galloyl-?2-D-glucopyranoside (12), are new compounds and other six, 1,6-di-O-galloyl-?2-D-glucopyranose (1), 1,4,6-tri-O-galloyl-?2-D-glucopyranose (2), 1,2-di-O-galloyl-?2-D-glucopyranose (3), 1,3-di-O-galloyl-?2-D-glucopyranose (4), 1,2,3-tri- O-galloyl-?±-D-glucopyranose (6) and methyl 3,4,6-tri-O-galloyl-?±-D-glucopyranoside (10), were synthesized for the first time in the present study. In in vitro MTT assay, 1-12 inhibited human cancer K562, HL-60 and HeLa cells with inhibition rates ranging from 64.2% to 92.9% at 100 ??g/mL, and their IC50 values were determined to be varied in 17.2-124.7 ??M on the tested three human cancer cell lines. In addition, compounds 1-12 inhibited murine sarcoma S180 cells with inhibition rates ranging from 38.7% to 52.8% at 100 ??g/mL in the in vitro MTT assay, and in vivo antitumor activity of 1 and 2 was also detected in murine sarcoma S180 tumor-bearing Kunming mice using taxol as positive control.

Tin-mediated regioselective benzylation and allylation of polyols: Applicability of a catalytic approach under solvent-free conditions

The first catalytic version of the stannylene-mediated benzylation and allylation of polyols is reported. The methodology is based on a simple solvent-free protocol that significantly advances, in terms of both experimental ease and synthetic scope, the a

Halide promoted organotin-mediated carbohydrate benzylation: Mechanism and application

In the present study, the mechanistic origin of the promoted organotin-mediated carbohydrate benzylation by halides was explored by the comparison of the activation ability of halides on benzylation of methyl β-d-galactoside. It was demonstrated that the

Regioselectivity of tin-mediated benzylation of glycoside

Regioselectivity of methyl α-D-glucopyranoside benzylation using dibutyltin dimethoxide (DBDM) as stannylating agent was probed, general factors affecting regioselectivity have been examined. The results show the O-2 position of glucoside has advantage of

Acceptor-influenced and donor-tuned base-promoted glycosylation

Base-promoted glycosylation is a recently established stereoselective and regioselective approach for the assembly of di- and oligosaccharides by using partially protected acceptors and glycosyl halide donors. Initial studies were performed on partially methylated acceptor and donor moieties as a model system in order to analyze the key principles of oxyanion reactivities. In this work, extended studies on base-promoted glycosylation are presented by using benzyl protective groups in view of preparative applications. Emphases are placed on the influence of the acceptor anomeric configuration and donor reactivities.

Hydroxy group acidities of partially protected glycopyranosides

A comprehensive acidity study of carbohydrate hydroxy groups has been carried out. Relative acidities (Ke) were determined spectrophotometrically for partially methylated methyl α-D- glycopyranosides. Apparently, the acidity is strongly affected by intramolecular hydrogen bonding as well as stereochemistry and solvation. By comparison with pKe and pKa values of aliphatic alcohols and polyols the first estimation of the pKa values for partially protected glycopyranosides was obtained. These findings contribute to the understanding of the relative reactivities of carbohydrate hydroxy groups.

Defining oxyanion reactivities in base-promoted glycosylations

Saccharide oxyanions obtained by base treatment could be employed in glycosylation to give oligosaccharides with high stereo- and regioselectivities.