1290130-76-5Relevant academic research and scientific papers
D-Glucose based syntheses of β-hydroxy derivatives of l-glutamic acid, l-glutamine, l-proline and a dihydroxy pyrrolidine alkaloid
Kumar, K. S. Ajish,Chattopadhyay, Subrata
, p. 19455 - 19464 (2015)
The β-hydroxy derivatives of l-glutamic acid, l-glutamine and l-proline, useful for peptide/protein studies, were synthesized starting from d-glucose. The C2 carbon in d-glucose provided the carboxylic acid functionality, while the amino and β-hydroxy groups of the amino acids were amenable from the C3 and C4 hydroxy groups of the sugar, respectively. The key intermediate with appropriate carbon framework of the target molecules was constructed by homologation of a suitable azido-d-glucofuranose derivative using the Arndt-Eistert reaction. This journal is
Total synthesis of natural cis-3-hydroxy-l-proline from d-glucose
Kalamkar, Navnath B.,Kasture, Vijay M.,Dhavale, Dilip D.
supporting information; experimental part, p. 6745 - 6747 (2011/02/25)
Synthesis of cis-3-hydroxy-l-proline from d-glucose is reported. The methodology involves conversion of d-glucose into N-benzyloxycarbonyl-γ- alkenyl amine which on 5-endo-trig-aminomercuration gave the pyrrolidine ring skeleton with sugar appendage in 25% yield. Alternatively, N-benzyloxycarbonyl- γ-alkenyl amine on hydroboration-oxidation, mesylation and intramolecular SN2 cyclisation afforded pyrrolidine ring compound in high yield. Hydrolysis of 1,2-acetonide functionality, NaIO4 cleavage followed by oxidation of an aldehyde into acid and hydrogenolysis afforded cis-3-hydroxy-l-proline in overall 29% yield from d-glucose.
