4356-78-9

Upstream product

• 88567-49-1 6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose 
• 67525-68-2 4'-Methoxyphenyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 75-36-5 acetyl chloride 
• 2872-65-3 p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 88567-49-1 6-O-acetyl-2,3,4,-tri-O-benzyl-α-D-glucopyranose 
• 10548-46-6 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose 
• 120403-27-2 phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 4356-77-8 acetyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 61277-56-3 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α/β-D-galactopyranose 
• 787623-80-7 p-methylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 3150-20-7 4-methoxyphenyl β-D-glucopyranoside 

Downstream Products

• 120403-36-3 methyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranosyde 
• 120403-31-8 phenyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 120403-33-0 phenyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 120403-28-3 phenyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 38184-16-6 phenyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 134428-50-5 6-O-acetyl-1,2,3-tri-O-benzyl-4-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-5a-carba-α-D-glucopyranose 
• 134428-50-5 6-O-acetyl-1,2,3-tri-O-benzyl-4-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-5a-carba-α-L-glucopyranose 
• 85227-90-3 Acetic acid (2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6S)-2-((2S,3R,4S,5R,6R)-6-acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-3,5,6-tris-benzyloxy-tetrahydro-pyran-4-yloxy]-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester 
• 116730-78-0 Methyl O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1-6)-tri-O-benzoyl-α-D-glucopyranoside 
• 79705-35-4 (2,2,2-Trichlorethyl)-4-O-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-galactopyranosyl)-2,3-O-isopropyliden-α-L-rhamnopyranosid 
• 79705-34-3 (2,2,2-Trichlorethyl)-4-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-2,3-O-isopropyliden-α-L-rhamnopyranosid 
• 120403-35-2 O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranosyl chloride 
• 87216-71-5 O-(2,3,4-Tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranosyl azide 
• 87216-73-7 O-(2,3,4-Tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranosyl azide 

Relevant academic research and scientific papers

STABLE VACCINE AGAINST CLOSTRIDIUM DIFFICILE

The present invention relates to a synthetic saccharide of general formula (I) that is related to Clostridium difficile PS-II cell-surface polysaccharide and conjugate thereof. Said synthetic saccharide, said conjugate and pharmaceutical composition containing said synthetic saccharide or said conjugate are useful for prevention and/or treatment of diseases associated with Clostridium difficile. Furthermore, the synthetic saccharide of general formula (I) is useful as marker in immunological assays for detection of antibodies against Clostridium difficile bacteria.

One-pot α-glycosylation pathway via the generation in situ of α-glycopyranosyl imidates in N,N-dimethylformamide

Divergent pathways are disclosed in the activation of 2-O-benzyl-1-hydroxy sugars by a reagent combination of CBr4 and Ph3P, all of which afford one-pot α-glycosylation methods. When this reagent is used in CH2Cl2, the 1-hydroxy sugar is converted to the α-glycosyl bromide in a conventional way and leads to the one-pot α-glycosylation method based on a halide ion-catalytic mechanism. In either DMF or a mixture of DMF and CHCl3, however, alternative α-glycosyl species are generated. From the 1H and 13C NMR study of the products, as well as the reactions using Vilsmeier reagents [(CH3)2N+CHX]X- (X = Br and Cl), these were identified as cationic α-glycopyranosyl imidates having either Br- or Cl- counter ion. The cationic α-glycosyl imidate (Br-), derived specifically in the presence of DMF, is more reactive than the α-glycosyl bromide and thus is responsible for the accelerated one-pot α-glycosylation. The one-pot α-glycosylation methodology performed in DMF was assessed also with different types of acceptor substrates including tertiary alcohols and an anomeric mixture of 1-OH sugars.

Conversion of p-methoxyphenyl glycosides into the corresponding glycosyl chlorides and bromides, and into thiophenyl glycosides

p-Methoxyphenyl (pMP) β-D-glycopyranosides (Glc, Gal, GlcNPhth, GalNPhth, GlcNTroc, Galβ4Glc, Galα4Gal) were prepared from the corresponding 1-O-acetyl sugars in 79-90% yield, using boron trifluoride etherate as promoter. Treatment of the pMP glycosides with acyl chlorides or bromides in the presence of various Lewis acids gave the corresponding glycosyl chlorides and bromides in 81-98% yield. Treatment of the acyl-protected pMP glycosides with thiophenol and boron trifluoride etherate gave the corresponding thioglycosides in 80-100% yield and high (> 20:1) β/α selectivity. The stability of pMP glycosides was investigated against a series of reagents.

Synthesis and reactions of an α-D-glucopyranosyl)phenylacetylene

Silver tetrafluoroborate promoted addition of (phenylethynyl)tributylstannane to 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl chloride stereoselectively gave a crystalline (α-D-glucopyranosyl)phenylacetylene (4) in 73% yield. Compound 4 was epimerized

Inhibitors of endo-α-mannosidase. Part III. Congeners of 1-deoxy-3-O-(α-D-glucopyranosyl)-mannojirimycin modified in the glucose unit

The syntheses of congeners of 1-deoxy-3-O-(α-D-glucopyranosyl)-mannojirimycin (1), a strong inhibitor of the glycoprotein-processing endo-mannosidase, are described. The chemical modifications of 1 involved all monodeoxygenations and mono-O-methylations o

SYSTEMATIC CHEMICAL SYNTHESIS AND N.M.R. SPECTRA OF METHYL α-GLYCOSIDES OF ISOMALTO-OLIGOSACCHARIDES AND RELATED COMPOUNDS

Acid-catalyzed thiophenolysis of 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose and acetylation of the resulting phenyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside (4) gave phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside (5).Reaction of 5 with chlorine gave, stereospecifically, the corresponding β-glycosyl chloride, which was treated with 4 in the presence of silver perchlorate and 2,4,6-trimethylpyridine to afford phenyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside (17).Crystalline O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D- glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranosyl chloride, readily obtainable in a stereospecific manner from 17 by treatment with chlorine, was used as the key glycosyl (isomaltosyl) donor in the bockwise synthesis of methyl glycosides of isomalto-oligosaccharides, up to and including the octasaccharide.The methyl α-glycoside of isomaltotetraose fluorinated at C-6 of the terminal D glucopyranosyl group was prepared by using SnCl2-activated 2,3,4-tri-O-benzyl-6-deoxy-6-fluoro-α,β-D-glucopyranosyl fluoride as the glycosyl donor, a suitably protected methyl α-isomaltotrioside as the nucleophile, and silver perchlorate as the promoter.The n.m.r. spectra (1H- and 13C-) of numereous synthetic intermediates were analyzed and completely assigned by a variety of two-dimensional homo- and hetero-nuclear n.m.r.-spectroscopic techniques, and the final deprotected title oligosaccharides were characterized by 13C-n.m.r. data.Silver perchlorate-mediated glycosylation reactions involving β-glycosyl chlorides were high-yielding and showed high stereoselectivity for the formation of an α-(cis)-glycosidic linkage.The practical limitation of obtaining high isomalto-oligosaccharides in this way appears to lie solely in the separation technique applied for the resolution of the crude products formed.

SYNTHESIS OF METHYL 6"-DEOXY-6'-FLUORO-α-ISOMALTOSIDE AND OF THE CORRESPONDING TRISACCHARIDE

Methyl 6-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (5) was formed with high stereoselectivity when the condensation of methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyl (1) with 6-O-acetyl-2,3,4-tri-O-benzyl-α-

Bausteine von Oligosacchariden, XXIX. Synthese des Trisaccharids aus N-Acetylglucosamin, Galactose und Rhamnose einer O-determinanten Kette von Escherichia coli. Abhaengigkeit der Stereoselektivitaet der α-Glycosidsynthese von der Reaktivitaet des Pyranos

The mercury salt catalysed reaction of substituted α-D-galactosyl halides with the reactive 4-OH groups of the rhamnosides 18 and 19 were studied.The order of reactivity of the halides increases with the following substituents: O-acetyl O-glucosyl O-b