86427-98-7Relevant academic research and scientific papers
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.
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.
A New Method for Cleaving Carbohydrate Triphenylmethyl and Benzyl Ethers
Klemer, Almuth,Bieber, Michael,Wilbers, Hubert
, p. 1416 - 1421 (2007/10/02)
Carbohydrate triphenylmethyl and benzyl ethers are converted into their trimethylsilyl ethers by iodotrimethylsilane.The silyl ethers are hydrolysed to give partially free sugars.From multiple benzylated glycosides it is possible to remove selectively the primary benzyl group, under more vigorous conditions total debenzylation occurs.
Catalytic transfer hydrogenation of benzylic and styryl compounds with palladium/carbon and 2-propanol. Selective removal of O-benzyl groups from carbohydrate derivatives
Rao, Vanga S.,Perlin, Arthur S.
, p. 652 - 657 (2007/10/02)
2-Propanol is shown to be an effective hydrogen donor, in the presence of palladium/carbon, for catalytic transfer hydrogenation reactions of benzylic and styryl compounds, e.g., for the quantitative conversion of cinnamyl alcohol into 3-phenylpropanol.In the reduction of derivatives of cinnamic acid, decarboxylation also occurs.During the latter reaction, the phenyl group appears to function as an anchoring group for the palladium atom, because derivatives of phenylpropanoic acid are decarboxylated more readily than are those of phenylacetic acid.In hydrogenolysis reactions, aryl alcohols undergo disproportionation whereas benzyl ethers, represented by O-benzyl and related derivatives of carbohydrates, are smoothly cleaved.Although 2-propanol is less reactive as a hydrogen donor than formic acid, it exhibits greater selectivity, as illustrated by relative rates of hydrogenolysis of O-benzyl and O-benzylidene substituents.The use of alumina-supported palladium is more effective than palladium/carbon for promoting stepwise removal of O-benzyl substituents, as shown by the preparation of methyl 2-O-benzyl- and -3-O-benzyl-α-D-glucopyranoside from the 2,3-di-O-benzyl derivative.A possible relationship between the orientation of O-benzyl groups and the chemical shift differences between the diastereotopic benzylic protons is decribed.
