140397-49-5

Upstream product

• 113019-43-5 2,6-Anhydro-3,4,5,7-tetra-O-benzyl-aldehydo-D-glycero-D-ido-heptopyranose 
• 89064-71-1 β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 91738-16-8 1,3-Diphenyl-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-imidazolidine 
• 154172-46-0 2-((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(thiazol-2-yl)-tetrahydro-2H-pyran-2-yl)thiazole 
• 491838-02-9 1-bis(methylthio)methyl-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 83615-64-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylformaldehyde 
• 215510-13-7 1-(β-D-glucopyranosyl)propan-2-one 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 100-39-0 benzyl bromide 
• 140461-63-8 (2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-propa-1,2-dienyl-tetrahydro-pyran 
• 85422-85-1 1-Deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl cyanide 
• 1056028-53-5 (E)-1-phenyl-2-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)ethene 
• 82659-59-4 3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene 
• 188819-43-4 (2R,3R,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-carbonitrile 

Downstream Products

• 136088-98-7 methyl 3-(2,3,4,6-O-tetrabenzyl-β-D-glucopyranosyl)propenoate 
• 197229-39-3 (3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-5-[(Z)-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 167102-63-8 (R)-N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-oxo-2-butanone 
• 213828-84-3 6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,4-dideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-arabino-D-manno/D-altro-3-undeculose 
• 347382-95-0 ((2S,3R,6S)-2-Ethoxy-6-hydroxymethyl-3,6-dihydro-2H-pyran-3-yl)-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methanol 
• 481667-83-8 (2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbaldehyde oxime 
• 556054-15-0 (1S,5R)-3-C-[(1R)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one 
• 608530-04-7 1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-3-phenyl-prop-2-yn-(1R)-ol 
• 608530-06-9 1-(2,3,4,6-tetra-O-benzyl-D-gluco-β-C-pyranosyl)-3-phenyl-prop-2-yn-(1S)-ol 
• 682807-87-0 [(Z)-1-Methoxy-2-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane 

Relevant academic research and scientific papers

C-MANNOSIDE COMPOUNDS USEFUL FOR THE TREATMENT OF URINARY TRACT INFECTIONS

Disclosed herein are new C-mannoside compounds and compositions and their application as pharmaceuticals for the treatment of human disease. Methods of inhibition of FimH activity in a human subject are also provided for the treatment diseases such as urinary tract infection.

C-GLYCOSIDE COMPOUNDS USEFUL FOR TREATING DISEASE

The present invention relates to mannoside derivative compounds useful as inhibitors of FimH and methods for the treatment or prevention of urinary tract infection.

Antivirulence C-Mannosides as Antibiotic-Sparing, Oral Therapeutics for Urinary Tract Infections

Gram-negative uropathogenic Escherichia coli (UPEC) bacteria are a causative pathogen of urinary tract infections (UTIs). Previously developed antivirulence inhibitors of the type 1 pilus adhesin, FimH, demonstrated oral activity in animal models of UTI but were found to have limited compound exposure due to the metabolic instability of the O-glycosidic bond (O-mannosides). Herein, we disclose that compounds having the O-glycosidic bond replaced with carbon linkages had improved stability and inhibitory activity against FimH. We report on the design, synthesis, and in vivo evaluation of this promising new class of carbon-linked C-mannosides that show improved pharmacokinetic (PK) properties relative to O-mannosides. Interestingly, we found that FimH binding is stereospecifically modulated by hydroxyl substitution on the methylene linker, where the R-hydroxy isomer has a 60-fold increase in potency. This new class of C-mannoside antagonists have significantly increased compound exposure and, as a result, enhanced efficacy in mouse models of acute and chronic UTI.

Synthesis of β-C-Glycopyranosyl Aldehydes and 2,6-Anhydro-heptitols

A convenient route has been developed for the diastereoselective synthesis of β-C-glycopyranosyl aldehydes from d-glucose, d-mannose, and d-galactose. The key step in the synthesis of C-glycosyl aldehydes is the aryl driven reductive dehydration on 1-phen

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

The present invention encompasses compounds and methods for treating and preventing bacterial infections specifically urinary tract infections and those caused by bacteria containing type 1 pili and FimH. The present invention also encompasses compounds and methods for treating inflammatory bowel disease specifically Crohn's Disease.

Preparation of 1-C-glycosyl aldehydes by reductive hydrolysis

Reductive hydrolysis of various protected glycosyl cyanides was carried out using DIBAL-H to form aldimine alane intermediates which were then hydrolyzed under mildly acidic condition to provide the corresponding aldehyde derivatives. While 1-C-formyl gly

New and general synthesis of β-C-glycosylformaldehydes from easily available β-C-glycosylpropanones

A highly effective method for the introduction of a formyl group at the anomeric position of pyranosides was developed via enolisation of β-C-d-glycopyranosylpropan-2-one using thermodynamic conditions then oxidative cleavage of the more substituted doubl

A convenient new route to protected and free 2,6-anhydro-d-glycero-d-gulo- heptoses (1-formyl-β-D-glucopyranosides)

A new and efficient process has been developed for the synthesis of 1-formyl-β-glucopyranosides from D-glucose.

Multigram scale synthesis of formyl tetra-O-benzyl-β-D-C-glucopyranoside using benzothiazole as a formyl group equivalent

The addition of 2-lithiobenzothiazole to D-gluconolactone followed by deoxygenation of the resulting ketose affords a mixture of benzothiazolyl α- and β-D-glucopyranoside; treatment of this mixture with sodium methoxide gives the β-anomer from which the title aldehyde is obtained in a pure form by transformation of the benzothiazole ring into the formyl group.

An efficient diastereoselective synthesis of β-1-formyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside

A diastereoselective synthesis of β-1-formyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside in four steps, using an umpolung Seebach reaction is described.