143615-35-4

Upstream product

• 74666-83-4 S-ethyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 38184-10-0 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 131531-70-9 4-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 139903-48-3 phenyl-2,3,4,6-tetra-O-benzyl-1-seleno-β-D-galactopyrannoside 
• 53081-25-7 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 25878-60-8 D-galactose pentaacetate 
• 100-39-0 benzyl bromide 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 108-93-0 cyclohexanol 
• 744246-05-7 2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 2021-84-3 α-galactosyl fluoride 
• 530-26-7 D-Mannose 

Downstream Products

• 128745-64-2 2,4-dimethylpentan-3-yl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 128745-65-3 2,4-dimethylpentan-3-yl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 70849-14-8 (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(3S,5S,8R,9S,10S,13R,14S,17R)-17-(1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran 
• 70849-14-8 (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(3S,5S,8R,9S,10S,13R,14S,17R)-17-(1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran 
• 128820-59-7 cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 128820-60-0 cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 117841-67-5 6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 117841-66-4 6-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 129894-49-1 cyclohexyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 129894-48-0 cyclohexyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 183954-67-8 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 267890-72-2 n-octyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 221678-94-0 Phenyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-1-seleno-α-D-mannopyranoside 
• 250273-70-2 4-acetyl-1,5-dibenzyloxy-3-hydroxy-2-C-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)benzene 

Relevant academic research and scientific papers

Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent

This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF6 as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF6 are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectively scavenged by Zn(II) to generate benign salts.

Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride

This study describes a new convenient method for the photocatalytic generation of glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%-97%, and it was applied in continuous flow to accomplish fluorination on an 7.7 g scale and 93% yield.

Blue Light Photocatalytic Glycosylation without Electrophilic Additives

Photocatalytic formation of glycosidic bonds employing stable and readily accessible O-glycosyl derivatives of 2,2,6,6-tetramethylpiperidin-1-ol is presented that employs an iridium-based photocatalyst and blue LEDs. The reaction proceeds at room temperature and in the absence of additives other than 4 ? molecular sieves. Stereoselectivities are modest but nevertheless dependent on the anomeric configuration of the donor, suggesting a substantial degree of concerted character.

Total synthesis of mangiferin, homomangiferin, and neomangiferin

Total synthesis of mangiferin, homomangiferin, and neomangiferin, three C-glycosyl xanthone natural products with a wide spectrum of pharmacological effects, has been achieved starting from 2,3,4,6-tetra-O-benzyl-α/β-d-glucopyranose. The key steps involve a stereoselective Lewis acid promoted C-glycosylation of protected phloroglucinol with tetrabenzylglucopyranosyl acetate and a highly regioselective base-induced cyclization for the construction of the core xanthone skeleton.

MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS

The present invention relates to compounds useful for the treatment or prevention of bacteria infections. These compounds have formula (I). The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. Finally, the invention provides processes for making compounds of the invention.

Glycosyl fluorides from n-pentenyl-related glycosyl donors-application to glycosylation strategies

n-Pentenyl glycosides (NPGs) and n-pentenyl orthoesters (NPOEs) have been transformed into glycosyl fluorides by a variety of methods. In the case of NPGs, Barluenga's reagent, bis(pyridinium)iodonium(I)tetrafluoroborate (IPy 2BF4),

Synthesis of glycosyl fluorides from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using aminodifluorosulfinium tetrafluoroborates

Glycosyl fluorides can be synthesized from thio-, seleno-, and telluroglycosides and glycosyl sulfoxides using the aminodifluorosulfinium tetrafluoroborate reagents Xtalfluor-E and -M, with or without added N-bromosuccinimide. Mechanistic studies provide evidence that fluoride is delivered from the tetrafluoroborate counterion.

Direct C-glycosylation of organotrifluoroborates with glycosyl fluorides and its application to the total synthesis of (+)-varitriol

A mild, stereoselective, and quick approach to accessing alkynyl and alkenyl C-glycosides via BF3?Et2O promoted coupling of organotrifluoroborates and glycosyl fluorides is reported. The application of this method was further demonstrated by the concise and efficient total synthesis of (+)-varitriol in only seven steps.

Silver(I) tetrafluoroborate as a potent promoter for chemical glycosylation

We have identified silver tetrafluoroborate (AgBF4) as an excellent promoter for the activation of various glycosyl donors including glycosyl halides, trichloroacetimidates, and thioimidates. Easy handling and no requirement for azeotropic dehydration prior to application makes AgBF4 especially beneficial in comparison to the commonly used AgOTf. Selective activation of glycosyl halides or thioimidates over thioglycosides or n-pentenyl glycosides, including simple sequential one-pot syntheses, has also been demonstrated. Versatility of glycosyl thioimidates was further explored by converting these intermediates into a variety of other classes of glycosyl donors.

ALPHA-GALACTOSYLCERAMIDE ANALOGS, THEIR METHODS OF MANUFACTURE, INTERMEDIATE COMPOUNDS USEFUL IN THESE METHODS, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

The invention relates to α-galactoceramide analogs, their methods of manufacture, intermediate compounds useful in these methods. It also relates to pharmaceutical compositions containing the α-galactoceramide analogs. The methods of manufacture of the invention involve the use of unsaturated intermediate compounds which enable to synthesize α-galactoceramide analogs by a mere metathesis reaction. The α-galactoceramide analogs of the invention are useful as active ingredients of pharmaceutical compositions, particularly in pharmaceutical compositions having anti-cancerous properties.