120444-53-3

Upstream product

• 120403-26-1 phenyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 498-07-7 levoglucosan 
• 100-44-7 benzyl chloride 
• 88567-49-1 6-O-acetyl-2,3,4,-tri-O-benzyl-α-D-glucopyranose 
• 120403-27-2 phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 88567-49-1 6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose 
• 61277-56-3 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α/β-D-galactopyranose 
• 10548-46-6 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose 

Downstream Products

• 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 
• 120403-31-8 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 
• 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 

Relevant academic research and scientific papers

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.

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.

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