1258282-08-4Relevant academic research and scientific papers
Copper mediated iodoacetoxylation and glycosylation: Effective and convenient approaches for the stereoselective synthesis of 2-deoxy-2-iodo glycosides
Battina, Suresh Kumar,Kashyap, Sudhir
, p. 811 - 814 (2016)
Copper(II) triflate catalyzed stereoselective glycosylation of 2-iodo-glycosyl acetate donor is reported. Anomeric activation of 2-deoxy-1-O-acetyl sugar employing Cu(OTf)2 found to be an attractive as well effective alternative reagent to the most frequently used triflic acid (TfOH) source such as TMSOTf or TBSOTf. Scope of the reaction was explored for various aglycones. This protocol involves simple reaction operation, employs less expensive and non-toxic reagent system, and enables the stereoselective preparation of 2-deoxy-2-iodo-glycosides. Furthermore, CuI/NaIO4 in the presence of AcOH at ambient temperature promoted the regioselective iodoacetoxylation of various glycals to access 2-iodo-glycosyl acetates.
A Rapid and Diastereoselective Synthesis of 2-Deoxy-2-iodo-α-glycosides and its Mechanism for Diastereoselectivity
Yuan, Wenjiao,Liu, Yali,Li, Chunbao
supporting information, p. 1975 - 1978 (2017/09/13)
Reductive deiodination of 2-deoxy-2-iodo-glycoside is an efficient and practical approach for the synthesis of 2-deoxyglycosides, which are moieties of bioactive compounds. However, inseparable diastereoisomers are usually formed in the preparation of 2-deoxy-2-iodo-glycosides via glycosylation of glycals with alcohols using current methods. To overcome this problem, a rapid and diastereoselective transformation of glycals and alcohols into 2-deoxy-2-iodo-α-glycosides enabled by I 2 /PhI(OAc) 2 has been developed. 14 glycals, derived from 13 monosaccharides and one disaccharide, diastereoselectively yielded α-glycosides. Only in two cases the diastereoselectivity of the glycosylation was poor. The yields of glycosylation range from 73% to 95%, and the reactions are finished in only five minutes. Investigations for better diastereoselectivity by comparing I 2 /Ph(OAc) 2 - with I 2 /Cu(OAc) 2 -mediated glycosylations using UV analysis have been conducted.
An efficient method for the selective synthesis of 2-deoxy-2-iodo- glycosides by O-glycosidation of d-glucal using I2-Cu(OAc) 2
Sirion, Uthaiwan,Purintawarrakun, Sittidate,Sahakitpichan, Poolsak,Saeeng, Rungnapha
experimental part, p. 2401 - 2407 (2010/11/18)
An efficient and convenient method for the synthesis of 2-deoxy-2-iodo-O-glycosides from tri-O-acetyl-d-glucal with various alcohols by using I2-Cu(OAc)2 is described. The 21 examples of corresponding glycosides were obtained in high
Convertible formation of different glycoside using molecular iodine
Saeeng, Rungnapha,Sirion, Uthaiwan,Sirichan, Yada,Trakulsujaritchok, Thanida,Sahakitpichan, Poolsak
experimental part, p. 2569 - 2580 (2011/04/22)
The observation of convertible formation between 2-deoxy-2-iodo-O- glycosides and 2,3-unsaturated glycoside was described. The selective formation of 2-deoxy-2-iodo-O-glycosides was found from the reaction of D-glucal with iodine in the excess alcohol acceptor or the addition of ceric ammonium nitrate as additive while the addition of a stoichiometric amount of alcohol in solvent favored 2,3-unsaturated glycosides formation. The Japan Institute of Heterocyclic Chemistry.
