114967-50-9Relevant academic research and scientific papers
High-Yield Syntheses of Tetra-O-benzyl-α-D-glucopyranosyl bromide and Tetra-O-pivaloyl-α-D-glucopyranosyl bromide and their Advantage in the Koenigs-Knorr Reaction
Presser, Armin,Kunert, Olaf,Poetschger, Irmgard
, p. 365 - 374 (2006)
Several improved approaches for the preparation of tetra-O-benzyl-α- D-glucopyranosyl bromide and tetra-O-pivaloyl-α-D-glucopyranosyl bromide are discussed. The importance of these compounds, which are useful glycosyl donors, was demonstrated by successful preparation of cholesteryl glucopyranosides in an almost neutral medium without the formation of orthoesters. In addition, accurate 1H and 13C NMR resonance assignments of the synthesized cholesteryl glycosides were performed by 2D NMR spectroscopy. Springer-Verlag 2006.
A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on the stereoselectivity
Sasaki, Kaname,Matsumura, Shuichi,Toshima, Kazunobu
, p. 7043 - 7047 (2004)
The glycosidations of glucopyranosyl fluoride and alcohols using an ionic liquid containing a protic acid effectively proceeded under mild conditions to afford the corresponding glycosides in good to high yields. The stereoselectivity of the glycosidation
Trichloroacetimidates as Glycosyl Donors in Recyclable Ionic Liquids
Poletti, Laura,Rencurosi, Anna,Lay, Luigi,Russo, Giovanni
, p. 2297 - 2300 (2003)
The trichloroacetimidates of different glycopyranoses were glycosylated in ionic liquids with different acceptors, affording the corresponding glycopyranosides in fair to excellent yields and allowing to recycle the solvent without additional Lewis acid.
A visible light promoted O-glycosylation with glycosyl trichloroacetimidates using eosin Y as an organo photoacid
Li, Hongfang,Liu, Jiao,Ni, Guanghui,Wang, Haimei,Yin, Shan
, (2020)
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
Glycosylation with trichloroacetimidates in ionic liquids: Influence of the reaction medium on the stereochemical outcome
Rencurosi, Anna,Lay, Luigi,Russo, Giovanni,Caneva, Enrico,Poletti, Laura
, p. 7765 - 7768 (2005)
The glycosylation with trichloroacetimidates derived from different glycopyranoses bearing a nonparticipating group at C-2 was explored in different ionic liquids as solvents. The stereoselectivity of the reaction was significantly affected by the reactio
Direct dehydrative glycosylation catalyzed by diphenylammonium triflate
Hsu, Mei-Yuan,Lam, Sarah,Lin, Mei-Huei,Lin, Su-Ching,Wang, Cheng-Chung,Wu, Chia-Hui
supporting information, (2020/03/13)
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
Iibuchi, Naoto,Eto, Takahiro,Aoyagi, Manabu,Kurinami, Reiji,Sakai, Hayato,Hasobe, Taku,Takahashi, Daisuke,Toshima, Kazunobu
supporting information, p. 851 - 855 (2020/02/15)
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
Visible light promoted method for constructing O-glycoside bonds
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Paragraph 0028-0029, (2020/07/13)
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
Remote Participation during Glycosylation Reactions of Galactose Building Blocks: Direct Evidence from Cryogenic Vibrational Spectroscopy
Marianski, Mateusz,Mucha, Eike,Greis, Kim,Moon, Sooyeon,Pardo, Alonso,Kirschbaum, Carla,Thomas, Daniel A.,Meijer, Gerard,von Helden, Gert,Gilmore, Kerry,Seeberger, Peter H.,Pagel, Kevin
supporting information, p. 6166 - 6171 (2020/03/10)
The stereoselective formation of 1,2-cis-glycosidic bonds is challenging. However, 1,2-cis-selectivity can be induced by remote participation of C4 or C6 ester groups. Reactions involving remote participation are believed to proceed via a key ionic intermediate, the glycosyl cation. Although mechanistic pathways were postulated many years ago, the structure of the reaction intermediates remained elusive owing to their short-lived nature. Herein, we unravel the structure of glycosyl cations involved in remote participation reactions via cryogenic vibrational spectroscopy and first principles theory. Acetyl groups at C4 ensure α-selective galactosylations by forming a covalent bond to the anomeric carbon in dioxolenium-type ions. Unexpectedly, also benzyl ether protecting groups can engage in remote participation and promote the stereoselective formation of 1,2-cis-glycosidic bonds.
Gold(III)-Catalyzed Glycosylation using Phenylpropiolate Glycosides: Phenylpropiolic Acid, An Easily Separable and Reusable Leaving Group
Shaw, Mukta,Thakur, Rima,Kumar, Amit
, p. 589 - 605 (2019/01/14)
An efficient and operationally simple gold(III)-catalyzed glycosylation protocol was developed using newly synthesized benchtop stable phenylpropiolate glycosyl (PPG) donors. Gold(III)-catalyzed activation of PPGs proceeds well with various carbohydrate a
