194149-26-3

Upstream product

• 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

• 122672-65-5 methyl 2-deoxy-2-(2-ethoxy-2-oxoethyl)-4,6-O-(phenylmethylene)-α-D-ribohexopyranosid-3-ulose 
• 122674-58-2 methyl 4,6-O-benzylidene-2-deoxy-2-C-propynyl-α-D-ribo-hexopyranosid-3-ulose 
• 63598-31-2 methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 
• 121467-58-1 (2R,4aR,6S,7S,8aR)-6-Methoxy-7-methyl-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one 
• 101978-79-4 Methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside 
• 6752-48-3 methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 6752-48-3 methyl 2-deoxy-4,6-O-benzylidene-α-D-ribo-hexopyranoside 
• 583-03-9 1-Phenyl-1-pentanol 
• 213829-10-8 methyl 2,4-di-O-benzoyl-α-D-mannopyranoside 
• 883104-81-2 (2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one O-methyl-oxime 
• 869544-01-4 1,5-anhydro-4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-erythro-hex-1-en-3-ulose 
• 869544-08-1 methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-β-D-erythro-hex-3-ulopyranoside dimethyl ketal 
• 869544-06-9 methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-erythro-hex-3-ulopyranoside dimethyl ketal 
• 869544-11-6 methyl 4-O-benzoyl-6-cyano-2,6-dideoxy-β-D-erythro-hex-3-ulopyranoside dimethyl ketal 

Relevant academic research and scientific papers

Glycosylation catalyzed by a chiral bronsted acid

"Chemical equation presented" The use of a chiral Bronsted acid catalyst for the activation of trichloroacetimidate glycosyl donors has been demonstrated for the first time. In toluene the chirality of the acid catalyst is seen to influence the stereochem

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.

Organocatalysis for the acid-free O-arylidenation of carbohydrates

Methyl glycopyranosides of glucose, galactose, and mannose, their 2,3-di-O-benzyl-protected derivatives, as well as the unprotected sugars react with p-methoxybenzaldehyde dimethyl acetal (3) and with benzaldehyde dimethyl acetal (7) as reagents in the presence of thiourea 1 or squaramide 2 as the organocatalyst to afford regioselectively 4,6-O-arylidenated derivatives 5 and 8. With an excess amount of 3 or 7, diarylidenated derivatives are also obtained. In situ formation of acetals of type 3 and 7 from corresponding aldehydes 10 and 13 in the presence of an orthoester and organocatalyst 1 or 2 can be used to generate 5 and 8 directly from the aldehydes. Some substrates also lead to mixed orthoesters with this procedure. The reaction courses are discussed. A squaramide catalyzes the 4,6-O-arylidenation of glucose, mannose, and galactose with the use of arenecarbaldehyde dimethyl acetals or arenecarbaldehydes and orthoesters as the reagents. Glycoside derivatives also undergo this reaction. Copyright

Environmentally benign preparation of benzylidene acetal of carbohydrate derivatives in PEG 600

An environmentally benign preparation of benzylidene acetal of carbohydrate derivatives catalyzed by HClO4-SiO2 in PEG 600 as solvent has been developed. Yields were excellent in every case. Copyright Taylor & Francis Group, LLC.

Base-promoted reaction of methyl 4,6-O-benzylidene-3-deoxy-hexopyranosid-2- ulose and various arylamines

Reaction of methyl 4,6-O-benzylidene-3(2)-deoxy-hexopyranosid-2(3)-ulose (1) with various arylamines under Bargellini reaction conditions was investigated. A series of unique enaminoketones 3-12 was obtained unexpectedly under basic conditions in 52-72% y

One-pot catalytic glycosidation/Fmoc removal - An iterable sequence for straightforward assembly of oligosaccharides related to HIV gp120

The removal of a transient Fmoc protecting group can be simply performed by the addition of excess Et3N just after the accomplishment of a Bi(OTf)3-promoted glycosidation reaction. The obtained oligosaccharide can be directly employed as a glycosyl acceptor for further elongation of the saccharide. The preparation of biologically important, linear and branched mannans incorporated into HIV gp 120 demonstrates that the iteration of this one-pot sequence leads to a very straightforward oligosaccharide assembly.

Synthesis of DIvalent 2,2′-linked mannose derivatives by homodimerization

Several studies have implicated (1 → 2)-linked mannans as biologically relevant compounds. Recently, there has been a growing interest in the synthesis of multivalent carbohydrate assemblies due to their ability to target multiple receptors simultaneously. In the present work, a protective group strategy, based on the methodology originally developed by Crich, has been utilized for the homodimerization of olefinic carbohydrates, allowing a highly diastereoselective synthesis of some divalent structures. Furthermore, it is shown that divalent donors may undergo coupling reactions without losses in stereoselectivity or efficiency. The strategies described may potentially be applied to the synthesis of diverse neoglycoconjugates and oligosaccharides. Georg Thieme Verlag Stuttgart.

Synthesis of L-vancosamine derivatives from methyl α-D- mannopyranoside

Concise synthesis of L-vancosamine, the amino sugar constituent of vancomycin and other antibiotics, has been achieved. The key steps include (1) stereoselective addition of methylcerium reagent to oximino ether, and (2) stereoselective hydrogenation of 5

A simple and mild synthesis of a 4,5-cyclopropanated carbohydrate

The synthesis of a 4,5-cyclopropanated carbohydrate was achieved in five steps from methyl α-d-mannopyranoside under mild conditions that avoid the use of carbene chemistry.

Synthesis of N-acylated 7-amino-2,6,7-trideoxy-D-erythroheptopyranosides from methyl α-D-mannoside

Hexopyranoside methyl α-d-mannoside (8) was homologated to yield 7-(acylamino)-2,6,7-trideoxy-heptopyranosides 19-26. A crucial reaction step is the radical cleavage of benzylidene derivative 10 to obtain bromide 11. Since nucleophilic substitution of 11