764656-49-7Relevant academic research and scientific papers
One step stereoselective synthesis of oxazoline-fused saccharides and their conversion into the corresponding 1,2-cisglycosylamines bearing various protected groups
Dong, Sanfeng,Zhao, Yitian,Shi, Yulong,Xu, Zhijian,Shen, Jingshan,Jia, Qi,Li, Yiming,Chen, Kaixian,Li, Bo,Zhu, Weiliang
, p. 1580 - 1588 (2021)
Herein we disclosed a straightforward synthesis of oxazoline-fused saccharides (oxazolinoses) from peracetylated saccharides and benzonitriles under acidic conditions with stoichiometric amounts of water. The density functional theory (DFT) calculations have revealed the origin of the stereoselectivity and the key role of water in promoting the departure of the acetyl group at C-2. The resulting oxazolinoses can be concisely converted into the corresponding 1,2-cisglycosylamines bearing various protected groups, allowing the access to schisandrin derivatives.
One-pot synthesis of N-glycooxazolines, N-glycoaminooxazolines, and N-glycothiazolines from glycals
Reid, Erica M.,Vigneau, Edward S.,Gratia, Synthia S.,Marzabadi, Cecilia H.,De Castro, Michael
experimental part, p. 3295 - 3303 (2012/07/13)
Novel one-pot syntheses of N-glycooxazolines (N at C-1), N-glycoaminooxazolines, and N-glycothiazolines have been developed. Thus, the reaction of tri-O-benzyl-D-glucal or tri-O-benzyl-D-galactal with aryl amides, heteroaryl amides, thioamides, and substi
The preparation of 2-iodoamides from glucals and their further transformations into oxazolines
De Castro, Michael,Marzabadi, Cecilia H.
, p. 6501 - 6504 (2007/10/03)
2-Deoxy-2-iodo-glycosylamides have been prepared from a variety of protected d-glucals by their reaction with N-iodosuccinimide and amides. Benzyl protected 2-iodoamides, when treated with sodium hydride and 15-crown-5, gave stable C1 N-linked 2-glycooxaz
