5041-92-9

Upstream product

• 106-48-9 4-chloro-phenol 
• 604-69-3 β-D-glucose pentaacetate 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 78942-85-5 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-β-D-glucopyranose 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate 

Downstream Products

• 4756-30-3 p-chlorophenyl β-D-glucopyranoside 

Relevant academic research and scientific papers

Revisit of the phenol O-glycosylation with glycosyl imidates, BF 3·OEt2 is a better catalyst than TMSOTf

With BF3·OEt2 as the catalyst, the glycosylation of phenols with glycosyl trichloroacetimidates (or N-phenyl trifluoroacetimidates) bearing 2-O-participating groups leads to the desired 1,2-trans-O-glycosides in generally excellent yields without formation of the 1,2-cis-anomers. However, with TMSOTf as the catalyst, the outcomes of the corresponding phenol O-glycosylation are highly dependent on the nucleophilicity of the phenols; less nucleophilic is the phenol, higher amounts of the 1,2-cis-O-glycoside together with more side-products are generated. 1,2-Orthoesters have been found to be the major products at a low temperature (a higher temperature. BF 3·OEt2 is an effective catalyst to promote the conversion of 1,2-orthoesters into the corresponding 1,2-trans-O-glycosides. However, the 1,2-orthoesters could be converted into the dioxolenium triflate and glycosyl triflate in the presence of TMSOTf, these intermediates which might be in equilibrium with the glycosyl oxocarbenium related species lead to the final mixture of the α/β-O-glycosides and side-products.

Stereoselective single-step synthesis and X-ray crystallographic investigation of acetylated aryl 1,2-trans glycopyranosides and aryl 1,2-cis C2-hydroxy-glycopyranosides

Reported is an attractive and environmentally friendly method for the synthesis of the title compounds in moderate yield using inexpensive 1,2,3,4,6-penta-O-acetyl-β-d-gluco- and galactopyranoses as sugar donors, five different phenols as acceptors and H-β zeolite as the catalyst. The yield (23-28%) of aryl 3,4,6-tri-O-acetyl-α-d-glycopyranosides obtained in this single-step procedure is considerably higher than that obtained using previously reported methods. Treatment of an orthoacetate, 3,4,6-tri-O-acetyl- [1,2-O-(1-p-fluorophenoxyethylidene)]-α-d-glucopyranose, with p-fluorophenol under the same solvent-free reaction conditions also led to the formation of the title compounds in similar yield and composition. X-ray crystallographic analysis of phenyl 3,4,6-tri-O-acetyl-α-d-glucopyranoside and p-fluorophenyl 3,4,6-tri-O-acetyl-α-d-glucopyranoside showed that the molecular packing is stabilized by C-H...O, C-H...π and C-H...F interactions, in addition to regular hydrogen bonding patterns.

Stereoselectivity of reactions at the glycoside center of carbohydrates: VII. Synthesis of aryl α- and -β-D-glucopyranosides by Helferich, catalyzed by boron trifluoride etherate

13C NMR spectroscopy was used to study the stereoselectivity of glycosylation of phenols with the α and β anomers of penta-O-acetyl-D-glucopyranose, penta-O-trifluoroacetyl-D-glucopyranose, and 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-D-glucopyranose in the presence of boron trifluoride etherate at varied temperature, time, and catalyst amount. The boron trifluoride etherate-catalyzed reaction of penta-O-acetyl-β -D-glucopyranose and 2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-β -D-glucopyranose with phenols occurs with a high stereocontrol to give, depending on conditions, predominantly 1,2-cis- or 1,2-trans-aryl-glycosides. This reaction can be used for preparative synthesis of the α- and β-anomeric forms of glycosides of a wide range of phenols.

Solid-liquid phase transfer catalyzed novel glycosylation reaction of phenols

A facile and mild glycosylation reaction in solid-liquid two-phase system (powdered K2CO3/CHCl3) containing phase transfer catalyst was found to be efficient for preparation of glucosides of 2', 6'-dihydroxyacetophenone (1) and other various substituted phenols.

Glycosides. Part 1. New Synthesis of 1,2-trans O-Aryl Glycosides, via Tributyltin Phenoxides

A new method of glycosidation of phenols has been studied.The reaction of tributyltin phenoxides 2 with 1,2,3,4,6-penta-O-acetyl-D-hexopyranosides 3, 7 and 9, in the presence of tin tetrachloride is described.Glycosides 4, 8 and 10 have been isolated in g

Novel Synthesis of Aryl 2,3,4,6-Tetra-O-acetyl-D-glucopyranosides

The glucosidation of phenols with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl fluoride in the presence of BF3*OEt2 to give, predominantly, α-anomers has been studied.In the presence of an amine base, 1,1,3,3-tetramethylguanidine, however, enhanced β-selectivity was achieved.The former reaction provides a novel and useful synthesis of aryl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside whilst the latter is effective for the glycosidation of relatively hindered phenols.