57783-73-0

Upstream product

• 67553-26-8 methyl 2,6-di-O-allyl-3,4-di-O-benzyl-α-D-glucopyranoside 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 81561-88-8 (2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-methoxy-5-trityloxy-2-trityloxymethyl-tetrahydro-pyran 
• 233744-18-8 4-[4-((2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxymethyl)-phenylcarbamoyl]-butyric acid 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 591727-19-4 1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 67-56-1 methanol 
• 73045-75-7 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl chloride 
• 79218-89-6 methyl 2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranoside 
• 81561-88-8 (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-6-methoxy-5-trityloxy-2-trityloxymethyl-tetrahydro-pyran 
• 73395-14-9 methyl (R,R)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 100-44-7 benzyl chloride 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 

Downstream Products

• 94152-35-9 Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-methoxy-6-trifluoromethanesulfonyloxymethyl-tetrahydro-pyran-3-yl ester 
• 114244-45-0 Toluene-4-sulfonic acid (2R,3R,4R,5R,6S)-3,4-bis-benzyloxy-5-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 
• 171038-58-7 methyl 3,4-di-O-benzyl-6-bromo-6-deoxy-α-D-glucopyranoside 
• 170953-36-3 (1R,3S,4R,5R,6S)-5,6-dibenzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane 
• 14199-63-4 1-deoxymannojirimycin 
• 94119-06-9 (1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane 
• 94119-08-1 3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol 
• 94119-07-0 (1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane-5-carboxylic acid benzyl ester 
• 94119-05-8 Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-6-aminomethyl-4,5-bis-benzyloxy-2-methoxy-tetrahydro-pyran-3-yl ester 
• 1174578-68-7 methyl 3,4-di-O-benzyl-2,6-di-O-propargyl-α-D-glucopyranoside 
• 1291083-15-2 methyl 3,4-di-O-benzyl-2,6-di-O-{1-[(1(S)-carboxy-2-phenylethyl)]-4-methyl-1H-1,2,3-triazole-4-yl}-α-D-glucopyranoside 
• 1174578-70-1 methyl 3,4-di-O-benzyl-2,6-di-O-{1-[(1(S)-carboxy-2-p-hydroxyphenylethyl)]-4-methyl-1H-1,2,3-triazole-4-yl}-α-D-glucopyranoside 
• 1291083-14-1 methyl 3,4-di-O-benzyl-2,6-di-O-{1-[(1(S)-methoxycarbonyl-2-p-hydroxyphenylethyl)]-4-methyl-1H-1,2,3-triazole-4-yl}-α-D-glucopyranoside 
• 1291083-13-0 methyl 3,4-di-O-benzyl-2,6-di-O-{1-[(1(S)-methoxycarbonyl-2-phenylethyl)]-4-methyl-1H-1,2,3-triazole-4-yl}-α-D-glucopyranoside 

Relevant academic research and scientific papers

Four Different Regioisomeric Polycarbonates Derived from One Natural Product, d -Glucose

Strategies for the preparation of polycarbonates, derived from the natural product d-glucose, which have the potential to degrade back into their bioresorbable starting material and CO2, were developed. By employing established carbohydrate pro

Mannose-binding geometry of pradimicin A

Pradimicins (PRMs) and benanomicins are the only family of non-peptidic natural products with lectin-like properties, that is, they recognize D-mannopyranoside (Man) in the presence of Ca2+ ions. Coupled with their unique Man binding ability, t

β-Rhamnosides from 6-thio mannosides

Upon condensation of 6-thio-6-deoxy-mannosyl donors 1,2-cis products are obtained with a high degree of stereoselectivity. Subsequent reductive removal of the 6-thio functionality gives 1,2-cis rhamnosides. The 1,2-cis-selectivity can be rationalized with

Rapid assembly of gp120 oligosaccharide moieties via one-pot glycosidation-deprotection sequences

Mannosyl trihaloacetimidate donors equipped with a 2-O-Fmoc group can be effectively activated by catalytic Bi(OTf)3 in glycosidations. Despite the expected participating effect of the Fmoc group, the reaction solvent was found to be decisive f

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.

Sonochemistry: A powerful way of enhancing the efficiency of carbohydrate synthesis

Using sonication as a means of facilitating organic reactions in carbohydrate chemistry was explored under the conditions used for traditional organic synthesis. An array of representative reactions, including hydroxy group manipulation (acylation, protection/deprotection, acyl group migration), thioglycoside synthesis, azidoglycoside synthesis, 1,3-dipolar cycloaddition and reductive cleavage of benzylidene, commonly used in the synthesis of carbohydrate derivatives was examined. A series of glycosylation reactions that employ thioglycosides, glycosyl trichloroacetimidate, glycosyl bromide and glycosyl acetate as the glycosyl donors was also examined. Our results demonstrate that sonication can significantly shorten the reaction time, enhance the reactivity of reactant and lead to superior yield and excellent stereoselectivity. More importantly, a general protocol of glycosylation may finally be developed. Sonication is compatible to the conditions used for traditional organic synthesis. We believe that sonication can also be applied to other areas of synthetic processes.

Synthesis of novel mannose-based crown ethers

A novel class of chiral crown ether analogues incorporating carbohydrate subunits can be easily prepared from methyl α-D-mannopyranoside. By a short reaction sequence involving either alkylations using a dibutylstannane intermediate or by phase transfer c

Efficient synthesis of man2, man3, and man 5 oligosaccharides, using mannosyl iodide donors

A highly efficient protocol for making Man3 and Man5 oligosaccharides with use of orthogonally protected glycosyl iodide donors has been developed. Glycosylation of a C-2-O-acetyl mannosyl iodide donor in the presence of silver trifl

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.