114179-84-9

Upstream product

• 2280-44-6 D-Glucose 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 3282-30-2 pivaloyl chloride 

Downstream Products

• 856214-68-1 4-chloro-N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)benzylideneamine 
• 845513-59-9 2-hydroxy-N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)benzylideneamine 
• 856214-72-7 3-nitro-N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)benzylideneamine 
• 856214-71-6 4-nitro-N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)benzylideneamine 
• 676144-17-5 C₆₅H₉₃F₅O₁₃S 
• 81058-27-7 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide 
• 1068437-14-8 4-phenyl-1-[2,3,4,6-tetrakis-O-(2,2-dimethylpropanoyl)-D-glucopyranosyl]-1H-[1,2,3]triazole 
• 1251910-93-6 4-(4-bromophenyl)-1-[2,3,4,6-tetrakis-O-(2,2-dimethylpropanoyl)-D-glucopyranosyl]-1H-[1,2,3]triazole 
• 1251910-95-8 4-(4-methylphenyl)-1-[2,3,4,6-tetrakis-O-(2,2-dimethylpropanoyl)-D-glucopyranosyl]-1H-[1,2,3]triazole 

Relevant academic research and scientific papers

Novel glycosyl pyridyl-triazole@palladium nanoparticles: Efficient and recoverable catalysts for C-C cross-coupling reactions

We report the development of a series of glycosyl pyridyl-triazole@palladium nanoparticles (GPT-Pd) which were synthesized by the reaction of azidoglycosides with 2-ethynylpyridine via click chemistry. These palladium nanoparticles were obtained in high yields and were fully characterized by 1H and 13C NMR, elemental analysis, transmission electron microscopy, and thermogravimetric analysis. The single crystal structure of GPT-Pd catalyst 5c was determined to show that the glycosyl pyridyl-triazole coordinated with palladium in a bidentate (N,N) coordination mode. Their use in palladium-catalyzed C-C coupling reactions such as Suzuki-Miyaura coupling, Heck reaction and Sonogashira reaction achieved quantitative production under mild conditions. Furthermore, the catalysts can be easily separated from the reaction mixture and the catalytic activity remained unchanged even after 8 successive catalytic cycles. This journal is

Total synthesis and structural revision of the alkaloid IncargranineB

Seeing double: Consideration of the biosynthetic origins of incargranineB, which was originally assigned an unprecedented indolo[1.7]naphthyridine structure, led to the proposal of a dipyrroloquinoline framework as a more biosynthetically feasible structure (see scheme; Piv=pivaloyl). This hypothesis was validated by a short biomimetic synthesis of incargranineB.

A Highly Stereoselective Synthesis of β-Glucosides from Pentaacylglucopyranose and Alkyl Silyl Ether by the Use of a Catalytic Amount of Active Species Generated from Methyltrichlorosilane and SIlver Perchlorate

An efficient catalytic β-glycosylation reaction starting from pentaacylglucopyranose and alkyl silyl ether was performed using an active species generated from MeSiCl3 and AgClO4. 1-O-Acetyl-2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranose stereoselectively rea

Hafnium inspired activation of highly hindered anhydrides in the acylation of alcohols and polyols

A novel and highly efficient method for activating highly hindered acid anhydrides towards the acylation of alcohols and carbohydrate-derived polyols has been developed. This new method relies on the capacity of the hafnium triflate catalyst Hf(OTf)2 to activate highly hindered acid anhydrides, and to direct the acylation reaction. This new acylation protocol is mild and proceed at room temperature with low catalyst loading. The method is versatile and has been extended to different alcohol substrates with different steric encumbrance as well as carbohydrate-derived polyols to afford the corresponding ester products in good to excellent yields.

A five-extra valeryl-based pyran glucose preparation method

The invention discloses a method for preparing penta-pivaloyl glucopyranose. The method comprises the following steps: adding an organic solvent to glucose, and stirring and cooling; adding pivaloyl chloride, 4-dimethylaminopyridine and an acid-binding agent; reacting to synthesize penta-pivaloyl glucopyranose, wherein a reaction system formed by glucose, the organic solvent, pivaloyl chloride, 4-dimethylaminopyridine and the acid-binding agent can be mutually dissolved with water; adding water to the reaction system for quenching reaction after reaction is ended; and filtering, re-crystallizing and drying to obtain penta-pivaloyl glucopyranose. Compared with an existing process, the post-treatment method is simplified; the product loss in the treatment process is reduced; the quality of the product is improved; the yield of the product is improved; organic solvent extracting and washing operations are not carried out; the consumption of the organic solvent, acid and base is reduced; the operation is simple; and the harm to the environment is small.

Total Synthesis of Millingtonine

Millingtonine is a glycosidic alkaloid that exists as a pair of pseudo-enantiomeric diastereomers. Consideration of the likely biosynthetic origins of this unusual natural product has resulted in the development of a seven-step total synthesis. Results fr

Synthesis and Biological Evaluation of Novel Carbohydrate-Derived Derivatives of Erlotinib

(Table presented.). A series of novel carbohydrate-derived Erlotinib derivatives were prepared by the copper-catalyzed cycloaddition reaction of erlotinib with various azido-sugars. The structures of the newly synthesized compounds were characterized and their cytostatic effects evaluated in vitro on human cancer cell lines MDA-MB-231, HEPG-2, A549, and MCF-7 using an MTS assay. The novel erlotinib derivatives had the expected inhibitory effects on MDA-MB-231 and HEPG-2 cell llines. Among the compounds evaluated the carbohydrate-derived compounds 5b, 5d, 6a, and 6c had more potent activities against MDA-MB-231 or HEPG-2 than Erlotinib. Drug Dev Res, 2016.

Synthetic Method of 20 (S)-Ginsenoside Rh2

A synthetic method of 20(s)-ginsenoside Rh2, that is 20(S)-protopanaxdiol-3-O-β-D-glucopyranoside, is comprised of: protecting protopanaxdiol (A1) selectively first to produce monosubstituted protopanaxdiol (A2); and Glycosidating the monosubstituted protopanaxdiol with Glucopyranosyl donor in the presence of Lewis acid catalyst; Deprotecting the product; Then separating and purifying to obtain 20(s)-ginsenoside Rh2. The method is conducted under mild condition at low cost, and affords product with high stereoselectivity, high yield and purity. Therefore, the synthetic method of the present invention is suitable for production on large scale.