78153-79-4

Usage

InChI:InChI=1/C34H35FO5/c35-34-33(39-24-29-19-11-4-12-20-29)32(38-23-28-17-9-3-10-18-28)31(37-22-27-15-7-2-8-16-27)30(40-34)25-36-21-26-13-5-1-6-14-26/h1-20,30-34H,21-25H2/t30-,31-,32+,33-,34-/m1/s1

Upstream product

• 3866-62-4 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 220662-68-0 2-{[(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)oxy]methyl}benzoic acid 
• 38184-10-0 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 117841-64-2 (pent-4′-enyl) 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 365534-59-4 2'-(benzyloxycarbonyl)benzyl α-D-mannopyranoside 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 131531-70-9 4-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 62774-37-2 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 

Downstream Products

• 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 
• 121820-73-3 phenyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 184178-66-3 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 116113-70-3 isopropyl-O-2,3,4,6-tetra-O-benzyl-β-D-mannopyranose 
• 116113-69-0 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-isopropoxytetrahydro-2H-pyran 
• 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.

A dehydrative glycosylation protocol mediated by nonafluorobutanesulfonyl fluoride (NfF)

A new dehydrative glycosylation protocol that proceeds through selective activation of glycosyl hemiacetals with nonafluorobutanesulfonyl fluoride (NfF) has been disclosed. Contrary to the major classical glycosylation reactions that proceed under acidic

Vessel Effect in C–F Bond Activation Prompts Revised Mechanism and Reveals an Autocatalytic Glycosylation

Activation of C–F bonds under acidic conditions results in the formation of hydrogen fluoride as the reaction progresses. In the following communication, the effect of the vessel material on such reactions has been investigated and a significant differenc

Chemical glucosylation of pyridoxine

The chemical synthesis of pyridoxine-5′-β-D-glucoside (5′-β-PNG) was investigated using various glucoside donors and promoters. Hereby, the combination of α4,3-O-isopropylidene pyridoxine, glucose vested with different leaving and protecting groups and the application of stoichiometric amounts of different promoters was examined with regards to the preparation of the twofold protected PNG. Best results were obtained with 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl fluoride and boron trifluoride etherate (2.0 eq.) as promoter at 0 °C (59%). The deprotection was accomplished stepwise with potassium/sodium hydroxide in acetonitrile/water followed by acid hydrolysis with formic acid resulting in the chemical synthesis of 5′-β-PNG.

Deoxyfluorination with CuF2: Enabled by Using a Lewis Base Activating Group

Deoxyfluorination is a primary method for the formation of C?F bonds. Bespoke reagents are commonly used because of issues associated with the low reactivity of metal fluorides. Reported here is the development of a simple strategy for deoxyfluorination, using first-row transition-metal fluorides, and it overcomes these limitations. Using CuF2 as an exemplar, activation of an O-alkylisourea adduct, formed in situ, allows effective nucleophilic fluoride transfer to a range of primary and secondary alcohols. Spectroscopic investigations have been used to probe the origin of the enhanced reactivity of CuF2. The utility of the process in enabling 18F-radiolabeling is also presented.

Rapid Deoxyfluorination of Alcohols with N-Tosyl-4-chlorobenzenesulfonimidoyl Fluoride (SulfoxFluor) at Room Temperature

The deoxyfluorination of alcohols is a fundamentally important approach to access alkyl fluorides, and thus the development of shelf-stable, easy-to-handle, fluorine-economical, and highly selective deoxyfluorination reagents is highly desired. This work describes the development of a crystalline compound, N-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor), as a novel deoxyfluorination reagent that possesses all of the aforementioned merits, which is rare in the arena of deoxyfluorination. Endowed by the multi-dimensional modulating ability of the sulfonimidoyl group, SulfoxFluor is superior to 2-pyridinesulfonyl fluoride (PyFluor) in fluorination rate, and is also superior to perfluorobutanesulfonyl fluoride (PBSF) in fluorine-economy. Its reaction with alcohols not only tolerates a wide range of functionalities including the more sterically hindered alcoholic hydroxyl groups, but also exhibits high fluorination/elimination selectivity. Because SulfoxFluor can be easily prepared from inexpensive materials and can be safely handled without special techniques, it promises to serve as a practical deoxyfluorination reagent for the synthesis of various alkyl fluorides.

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.