58341-68-7

Upstream product

• 100-39-0 benzyl bromide 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 221002-70-6 methyl 2‐O‐benzoyl‐3‐O‐benzyl‐4,6‐O-benzylidene‐α‐D‐glucopyranoside 
• 100-44-7 benzyl chloride 
• 160529-97-5 methyl 2-O-benzoyl-3,6-di-O-benzyl-α-D-glucopyranoside 

Downstream Products

• 676265-74-0 2,5-anhydro-3,6-di-O-benzyl-4-deoxy-1,4-difluoro-1-O-methyl-D-talitol 
• 1352717-96-4 methyl 3,6-di-O-benzyl-2,4-di-O-methyl-α-D-glucopyranoside 
• 676265-76-2 2,5-anhydro-3,6-di-O-benzyl-4-deoxy-4-fluoro-aldehydo-D-talose 
• 221002-89-7 methyl 2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,6-di-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Carbohydrate-Derived Metal-Chelator-Triggered Lipids for Liposomal Drug Delivery

Liposomes are versatile three-dimensional, biomaterial-based frameworks that can spatially enclose a variety of organic and inorganic biomaterials for advanced targeted-delivery applications. Implementation of external-stimuli-controlled release of their cargo will significantly augment their wide application for liposomal drug delivery. This paper presents the synthesis of a carbohydrate-derived lipid, capable of changing its conformation depending on the presence of Zn2+: an active state in the presence of Zn2+ ions and back to an inactive state in the absence of Zn2+ or when exposed to Na2EDTA, a metal chelator with high affinity for Zn2+ ions. This is the first report of a lipid triggered by the presence of a metal chelator. Total internal reflection fluorescence microscopy and a single-liposome study showed that it indeed was possible for the lipid to be incorporated into the bilayer of stable liposomes that remained leakage-free for the fluorescent cargo of the liposomes. On addition of EDTA to the liposomes, their fluorescent cargo could be released as a result of the membrane-incorporated lipids undergoing a conformational change.

Iron(iii) chloride-tandem catalysis for a one-pot regioselective protection of glycopyranosides

Tandem catalysis by using iron(iii) chloride hexahydrate leads to carbohydrate building blocks displaying an orthogonal protecting group pattern as illustrated by the regioselective protection of trehalose and maltose disaccharides.

New method for regioselective glycosylation employing saccharide oxyanions

As an alternative concept for glycosylation, the prior activation of acceptor hydroxy groups for selective glycosidic bond formation, was investigated to give complex oligosaccharides. Oxyanions obtained from partially protected saccharides were glycosylated by employing glycopyranosyl halides, and the regiochemical results were studied. Initially, partially methylated methyl-α-D-glucopyranosides were used as a model system to study the underlying mechanistic principles of base-promoted glycosylation. High regioselectivities and stereospecific glycosidic bond formations were achieved, and the scope of the methodology was extended with different perbenzylated glycosyl donors.

Efficient procedure for reductive opening of sugar 4,6-O-benzylidene acetals in a microfluidic system

An efficient procedure for the reductive opening of 4,6-O-benzylidene acetals was established under microfluidic conditions. 4,6-O-Benzylidene acetals of the glucose, glucosamine, and galactose derivatives were selectively converted into the corresponding

Tandem catalysis for a one-pot regioselective protection of carbohydrates: The example of glucose

(Chemical Equation Presented) Fine-tuning the conditions for a tandem reaction using a single catalyst in a single reaction vessel leads to carbohydrate building blocks displaying different patterns of protecting groups (see picture). This process greatly simplifies the access to oligomers, as illustrated by the rapid assembly of a trisaccharide.

Direct and convenient method of regioselective benzylation of methyl α-D-glucopyranoside

A facile and convenient method for the direct preparation of methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside (2) by the regioselective benzylation of methyl α-D-glucopyranoside (1) with benzyl bromide in the presence of mild bases K2CO3 and KOH (1:1) withou

Fluorination of 2-hydroxy-hexopyranosides by DAST: Towards formyl C-glycofuranosides from equatorial-2-OH methyl hexopyranosides

Reaction of diversely configured and substituted, unbranched methyl D-hexopyranosides with the DAST in dichloromethane or acetonitrile led to normal substitution products and/or rearranged fluoro compounds (ring-contracted 2,5-anhydro-1-fluoro-1-O-methylhexitol derivatives, 2-methoxy-D-hexopyranosyl fluorides, and, for some 3-azido substrates, rearranged 2-azido-3-fluoro-D-hexopyranosides). When the reaction was performed in acetonitrile, the solvent participation as a nucleophile (Ritter reaction) was observed in one case. For a 2,4-unprotected 3-azido substrate, 2,3-dehydration and fluorination at C(4), the latter with epimerization, took place. 19F/1H and 19F/13C coupling constant values were systematically applied to discriminate between isomeric structures for fluorinated products, and for some, previously described, coming from five 3-branched-chain D- or L-hexopyranosides, thus discarding the previously reported structural assignment. From the synthetic point of view, the most outstanding result was the preparation of 2,5-anhydro-1-fluoro-1-O- methylhexitols, showing a latent formyl group functionality, a transformation, which was achieved in one case. A rationalization for the formation of the different types of product is also proposed.

Synthesis and nmr characterisation of methyl mono- and DI-0-α-L-rhamnopyranosyl-α-d-glucopyranosiduronic acids

The synthesis and NMR characterisation of methyl mono- and di-O-α-L-rhamnopyranosyl-α-D-glucopyranosiduronic acids 1-6 are described. Two commercial starting products were used: methyl α-D-glucopyranoside 7 for the preparation of 1 and 2, and methyl (R)-4,6-O-benzylidene-α-D-glucopyranoside 8 for 3-6. Oxidation reaction of the hydroxymethyl group of glucose to a carboxylic acid group was performed by sodium hypochlorite 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)-mediated procedure after the coupling reaction. Glycosylation was carried out using the trichloroacetimidate approach with trimethylsilyl trifluoromethanesulfonate (TMSOTf) as promoter, resulting in a completely stereoselective formation of the a glycosyl linkage.

REGIOSELECTIVE ALKYLATION via TRIALKYLSTANNYLATION: METHYL α-D-GLUCOPYRANOSIDE

Partial stannylation of methyl α-D-glucopyranoside with (Bu3Sn)2O, and subsequent alkylation with benzyl bromide, allyl bromide, and trityl chloride, afforded the 2,6-disubstituted derivative as one of major products in each case.