56632-55-4

Upstream product

• 108-93-0 cyclohexanol 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 13871-89-1 trimethylsilyl cyclohexyl ether 
• 78153-79-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl fluoride 
• 89025-46-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride 
• 89825-08-1 2,3,4,6-tetra-O-benzyl-1-O-trimethylsilyl-α,β-D-glucopyranose 
• 56632-56-5 cyclohexyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 129470-73-1 S-1-(1'-phenyl-1H-tetrazolyl) 2,3,4,6-tetra-O-benzyl-β-D-glucopyranose 
• 166733-02-4 S-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-N,N,N',N'-tetramethyl-N''-phenylphosphorodiamidimidothioate 

Relevant academic research and scientific papers

Metal-free glycosylation with glycosyl fluorides in liquid SO2

Liquid SO2 is a polar solvent that dissolves both covalent and ionic compounds. Sulfur dioxide possesses also Lewis acid properties, including the ability to covalently bind Lewis basic fluoride ions in a relatively stable fluorosulfite anion (FSO2?). Herein we report the application of liquid SO2 as a promoting solvent for glycosylation with glycosyl fluorides without any external additive. By using various temperature regimes, the method is applied for both armed and disarmed glucose and mannose-derived glycosyl fluorides in moderate to excellent yields. A series of pivaloyl-protected O- and S-mannosides, as well as one example of a C-mannoside, are synthesized to demonstrate the scope of the glycosyl acceptors. The formation of the fluorosulfite species during the glycosylation with glycosyl fluorides in liquid SO2 is proved by 19F NMR spectroscopy. A sulfur dioxide-assisted glycosylation mechanism that proceeds via solvent separated ion pairs is proposed, whereas the observed α,β-selectivity is substrate-controlled and depends on the thermodynamic equilibrium.

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

A visible light promoted O-glycosylation with glycosyl trichloroacetimidates using eosin Y as an organo photoacid

A photoacid catalyzed O-glycosylation of alcohols with glycosyl trichloroacetimidates in the presence of commercially available phenolic photoacids, fluorescein, 4′,5′-dibromo-fluorescein, and eosin Y under visible light irradiation by blue LEDs was devel

Visible light promoted method for constructing O-glycoside bonds

The invention discloses a visible light promoted method for constructing O-glycoside bonds. Glycosyl trichloroacetimidate is taken as a donor, and phenolic compounds are taken as a photocatalyst; a molecular sieve is added; and the O-glycoside bonds are g

Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2-Aryl-1,3-dithiane 1-Oxide?

A new dehydrative glycosylation reaction has been established by capitalizing on the comproportionation reaction of 2-aryl-1,3-dithiane 1-oxides promoted by triflic anhydride (Tf2O). By wedding the high potency of thiophilic promoter system with the step efficiency of dehydrative glycosylation, this reagent underwent facile intermolecular oxothio acetalization with C1-hemiacetal donor to install a temporary leaving group, rendering a transient electrophilic center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3-diol protection. Most importantly, this method further provided a fresh perspective for the application of sulfur chemistry to carbohydrate chemistry.

Direct dehydrative glycosylation catalyzed by diphenylammonium triflate

Methods for direct dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.

Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields. In addition, t

α-Selective glycosylations using glycosyl: N-(ortho-methoxyphenyl)trifluoroacetimidates

Six N-(o-methoxyphenyl)trifluoroacetimidate glycosyl donors have been synthesized and their role as glycosyl donors has been investigated. The donors were synthesized with complete -selectivity, except in one case, and were found to be stable. When Bi(OTf

Visible Light Enables Aerobic Iodine Catalyzed Glycosylation

A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.

Bimodal Glycosyl Donors Protected by 2- O-(ortho-Tosylamido)benzyl Group

A glucosyl donor equipped with C2-o-TsNHbenzyl ether was shown to provide both α- and β-glycosides stereoselectivity, by changing the reaction conditions. Namely, β-glycosides were selectively obtained when the trichloroacetimidate was activated by Tf2NH. On the other hand, activation by TfOH in Et2O provided α-glycosides as major products. This "single donor" approach was employed to assemble naturally occurring trisaccharide α-d-Glc-(1→2)-α-d-Glc-(1→6)-d-Glc and its anomers.