81348-24-5Relevant articles and documents
Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups
Cavedon, Cristian,Sletten, Eric T.,Madani, Amiera,Niemeyer, Olaf,Seeberger, Peter H.,Pieber, Bartholom?us
supporting information, p. 514 - 518 (2021/01/26)
The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction suffers from poor functional group compatibility and limits their use as a protecting group. The visible-light-mediated debenzylation disclosed here renders benzyl ethers temporary protective groups, enabling new orthogonal protection strategies. Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time can be reduced from hours to minutes in continuous flow.
Azetidine iminosugars from the cyclization of 3,5-Di- O -triflates of α-furanosides and of 2,4-Di- O -triflates of β-pyranosides derived from glucose
Lenagh-Snow, Gabriel M. J.,Araujo, Noelia,Jenkinson, Sarah F.,Martinez, R. Fernando,Shimada, Yousuke,Yu, Chu-Yi,Kato, Atsushi,Fleet, George W.J.
, p. 2142 - 2145 (2012/07/13)
Primary amines with either 3,5-di-O-ditriflates of α-furanosides or 2,4-di-O-triflates of β-pyranosides form bicyclic azetidines in high yield.
A simple, mild, and regioselective method for the benzylation of carbohydrate derivatives promoted by silver carbonate
Malik, Satish,Dixit, Vaibhav A.,Bharatam, Prasad V.,Kartha, K.P. Ravindranathan
experimental part, p. 559 - 564 (2010/10/04)
A simple, mild, and regioselective method has been developed for the selective benzylation and p-methoxybenzylation of carbohydrate derivatives in high yields using Ag2CO3 as the promoter. Benzylation of base-labile substrates, for w
Synthesis of positional thiol analogs of β-D-galactopyranose
Pei, Zhichao,Dong, Hai,Caraballo, Remi,Ramstroem, Olof
, p. 4927 - 4934 (2008/03/14)
Approaches toward the synthesis of thio-β-D-galactose derivatives are described. These compounds were prepared from the parent carbohydrates: D-galactose, methyl β-D-galactoside and methyl β-D-glucoside, respectively. It was found that not only the strategies of protecting group introduction and selective deprotection, but also the choices of solvent and nucleophilic reagent concentration were crucial to allow the efficient introduction of sulfur at different positions of the galactose ring. The effects from the solvent, the nucleophilic reagent concentration, and the protecting group patterns have been investigated. The results clearly show that ester protecting groups play highly important roles for the synthesis of thio-containing carbohydrates, requiring nonpolar solvents to suppress the neighboring group participation. For the Lattrell-Dax (nitrite-mediated) inversion reaction, employed in the synthetic route to the 2-thio-β-D- galactoside, intramolecular nucleophilic attack, as well as stronger stereospecific ester activation, are necessary to overcome hindrance from 4,6-O-benzylidene protection. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Galactose-phosphonates as mimetics of the sialyltransfer by trypanosomal sialidases
Busse, Heike,Hakoda, Mitsuru,Stanley, Matthew,Streicher, Hansjoerg
, p. 159 - 194 (2008/02/11)
In an attempt to find competitive inhibitors of the trans-sialidase of the pathogen Trypanosoma cruzi, we have synthesized conjugates of carbocyclic sialylmimetics (e.g., cyclohexenephosphonates) and galactose derivatives. A trans-sialidase inhibition ass
Synthesis of novel HIV-1 protease inhibitors based on carbohydrate scaffolds
Murphy, Paul V.,O'Brien, Julie L.,Gorey-Feret, Lorraine J.,Smith III, Amos B.
, p. 2259 - 2271 (2007/10/03)
The synthesis of peptidomimetic inhibitors of HIV-1 protease based on 6-deoxy-6-amino-β-D-glucopyranoside and 6-deoxy-6-amino-β-D-mannopyranoside scaffolds has been achieved. The inhibitors had IC50 values in the micromolar range. The results provide a platform for the development of more potent carbohydrate based inhibitors of HIV-1 and other aspartic proteases.
Novel features of acceptor recognition by β-(1 ← 4)- galactosyltransferase
Kajihara, Yasuhiro,Kodama, Hisashi,Endo, Tsuyoshi,Hashimoto, Hironobu
, p. 361 - 378 (2007/10/03)
In order to understand how β-(1→4)-galactosyltransferase recognizes its glycosyl acceptor, substrate specificities were investigated using synthetic 2-acetamido-2-deoxy-D-glucopyranose (N-acetylglucosamine) derivatives in which the 1-, 2-, 3-, 4-, and 6-p
Syntheses of tri- and tetrasaccharide fragments of the capsular polysaccharide of Streptococcus pneumoniae type 23F
Steijn, A. M. P. van,Jetten, M.,Kamerling, J. P.,Vliegenthart, J. F. G.
, p. 374 - 383 (2007/10/02)
The syntheses of two trisaccharides, being fragments of the capsular polysaccharide of Streptococcus pneumoniae type 23F (3-OPO32-)-β-D-Glcp-(1-4)--β-D-Galp-(1-OCH3) (1), α-L-Rhap-(1-2)-β-D-Galp-(1-4)-β-L-Rhap-(1-OCH3) (2) and t
