137344-41-3

Upstream product

• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 917-54-4 methyllithium 
• 75-24-1 trimethylaluminum 
• 75-11-6 diiodomethane 
• 1822-00-0 trimethylsilylmethyllithium 
• 133697-34-4 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 
• 131603-38-8 (5R,6R,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-1,4-dioxa-spiro[2.5]octane 
• 138811-41-3 ((3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester 
• 138760-57-3 3,4,5,7-Tetra-O-benzyl-1-deoxy-1-C-trimethylsilyl-D-gluco-2-heptulopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 917-64-6 methyl magnesium iodide 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 140658-50-0 (2R,3R,4S,5R,6R)-3,4,5-tris-benzyl-6-benzyloxymethyl-2-dichloromethyltetrahydro-2H-pyran-2-ol 

Downstream Products

• 352020-79-2 methyl O-(1'-C-methyl-2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-(1'->6)-2,3,4-tri-O-benzyl-α-D-glucoside 
• 133697-34-4 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 
• 140658-55-5 2-O-acetyl-3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulopyranose 
• 130632-55-2 2,3,4,6-tetra-O-benzyl-1-C-methyl-α-D-glucopyranosyl dimethylphosphinothioate 
• 946847-85-4 ethyl 3,4,5,7-tetra-O-benzyl-1,2-dideoxy-2-thio-α-D-gluco-hept-2-ulopyranoside 
• 892402-16-3 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-ulopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 951764-84-4 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-ulopyranosyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Stereocontrolled Synthesis of 2-Fluorinated C-Glycosides

A systematic study of the addition of C-based nucleophiles to fluorinated lactones based on 2-deoxy-2-fluoro-d-pyranoses is disclosed. This high yielding, α-selective process was found to be independent on the nature or configuration [(R)-C(sp3)–F, (S)-C(sp3)–F] of the substituent at C2. Representative, fluorinated analogues of Trehalose, Carminic acid, and the spirocyclic cores of Tofogliflozin and Papulacandin D are also reported. These glycomimics constitute a valuable series of 19F NMR active probes for application in structural biology.

MAGNETIC LABELING OF BACTERIA

The present invention provides novel methods of magnetically labeling a bacterial cell by contacting the call with an affinity ligand and subsequently contacting the cell with a magnetic agent, where the affinity ligand and magnetic agent include bioorthogonally reactive groups that can react with each other to form a covalent bond. Compounds, compositions, kits and applications of the method are also described.

Synthesis of N-aryl spiro-sulfamides as potential glycogen phosphorylase inhibitors

A new C-glucosylated spiro-sulfamide has been prepared and evaluated toward glycogen phosphorylase inhibition. The synthesis was carried out successfully by nucleophilic displacement of 1-O-tosyl or 1-deoxy-1-iodo-α-d-gluco- hept-2-ulopyranose tetra-O-benzylated derivative using aryl amines, followed by the formation of the corresponding cyclic sulfamide.

Synthesis of ketopyranosyl glycosides and determination of their anomeric configuration on the basis of the three-bond carbon-proton couplings

Anomeric pairs of ketopyranosyl glycosides with various substituents at Cα, Cβ and Cγ were synthesized from the corresponding thioglycosides, and the influence of the Cα-Cβ-Cγ-Hγ

Stereoselective C-allylation of 1-C-alkyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoses with allyltrimethylsilane

The reaction of 1-C-alkyl-2,3,4,6-tetra-O-benzyl-D-glucopyanoses with allyltrimethylsilane in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate gave the corresponding C-allylated C-alkyl glucopyranosides in good yields. This C

Addition of trialkylaluminum reagents to glyconolactones. Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline

Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected 1-C-Me GlcNAc oxazoline, a potential 1-C-Me GlcNAc donor.

An efficient synthesis of new 1′-C-methyl-α-O-disaccharides using 1-methylenesugars as the glycosyl donors

A series of new 1′-C-methyl-α-disaccharides were firstly synthesized by the directly Lewis acid-catalyzed O-glycosidation of 1-methylenesugars used as glycosyl donors. The O-glycosidation afforded stereospecifically the corresponding 1′-methyl-α-O-glycosides whose configurations were tentatively assigned by the NMR spectra, COSY and the C-H coupling constant 3JH-2′,Me-1′. The O-glycosidation of the acetyl protected 1-methylenesugars showed that the acetyl group at the C-2-O position was not effective to control the stereochemistry of the product by neighboring group participation because of the formation of a tertiary oxycarbenium ion as a stable intermediate.

A facile synthesis of 1′-C-alkyl-α-disaccharides from 1-C-alkyl-hexopyranoses and methyl 1-C-methyl-hexopyranosides

Direct O-glycosidations using the 1-C-alkyl-2,3,4,6-tetra-O-benzyl-hexopyranoses as the glycosyl donors were carried out with a catalytic amount (0.2 equiv.) of trimethylsilyl trifluoromethanesulfonate (TMSOTf). The glycosidations proceeded α-stereoselect

Studies on the synthesis of C-glycoside sulfones as potential glycosyl transferase inhibitors

β-C-Glycoside sulfoxides and sulfones were prepared by radical addition of thiol acetic acid to exocyclic glycals followed by deacetylation, S-alkylation, and selective oxidation. These compounds are representative examples of a new class of molecules designed to be glycosyl transferase inhibitors.