135186-64-0Relevant academic research and scientific papers
Intramolecular Metal-Free C(sp3)-H Activation Enables a Selective MonoO-Debenzylation of Fully Protected Aminosugars
González, Concepción C.,Herrera, Antonio J.,Santana, Andrés G.
, p. 16736 - 16752 (2021/12/06)
Carbamate-bearing benzylated aminosugars undergo an I2/I(III)-promoted intramolecular hydrogen atom transfer (IHAT) followed by a nucleophilic attack to provide polycyclic structures. Thus, suitably positioned benzyl ethers are surgically oxidized into the corresponding mixedN/O-benzylidene acetals, which can be conveniently deprotected under mild acidic conditions to grant access to selectivelyO-deprotected aminosugars amenable for further derivatization. The scope of this strategy has been proven with a series of furanosic and pyranosic scaffolds. Preliminary mechanistic studies, including Hammett LFER and KIE analyses, support a reaction pathway with nucleophilic cyclization as the rate-determining step.
Synthesis and evaluation of inhibitors of E. coli PgaB, a polysaccharide de-N-acetylase involved in biofilm formation
Chibba, Anthony,Poloczek, Joanna,Little, Dustin J.,Howell, P. Lynne,Nitz, Mark
, p. 7103 - 7107 (2012/10/08)
Many medically important biofilm forming bacteria produce similar polysaccharide intercellular adhesins (PIA) consisting of partially de-N-acetylated β-(1 → 6)-N-acetylglucosamine polymers (dPNAG). In Escherichia coli, de-N-acetylation of the β-(1 → 6)-N-
Synthesis and characterization of monosaccharide derivatives and application of sugar-based prolinamides in asymmetric synthesis
Agarwal, Jyoti,Peddinti, Rama Krishna
, p. 6390 - 6406,17 (2020/09/16)
For the first time, the β-anomer of N-acetylglucosamine derivative methyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (9b) was synthesized, isolated, and used in the synthesis of sugar-based primary amine 4b. Sugar-based primary amine 5a, a
Glucosamine-based primary amines as organocatalysts for the asymmetric aldol reaction
Agarwal, Jyoti,Peddinti, Rama Krishna
, p. 3502 - 3505 (2011/06/21)
Glucosamine derivatives have been synthesized starting from commercially available N-acetyl-D-glucosamine/glucosamine hydrochloride and have been employed successfully as efficient organocatalysts for the direct asymmetric aldol reaction between cyclohexa
2-Amino-2-deoxyglycoside derivatives via Hofmann rearrangement of 2-carbamoyl-2-deoxyglycosides
Mostowicz,Belzecki,Chmielewski
, p. 273 - 274 (2007/10/02)
Methyl 2-methoxy- and 2-tert-butoxycarbonylamino-2-deoxyglycosides were obtained from methyl 2-carbamoyl-2-deoxyglycosides via Hofmann rearrangement with sodium methoxide/bromine/methanol or sodium hydroxide/sodium bromite/methanol or lead tetraacetate te
