113574-79-1Relevant articles and documents
A Rapid and Diastereoselective Synthesis of 2-Deoxy-2-iodo-α-glycosides and its Mechanism for Diastereoselectivity
Yuan, Wenjiao,Liu, Yali,Li, Chunbao
, p. 1975 - 1978 (2017)
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.
Iodosobenzene diacetate-Iodine and IBX-Iodine: Reagent systems for the synthesis of diastereomerically enriched 2-deoxy-2-iodoglycosyl acetates and 2-deoxy-2-iodoglycosyl ortho-iodobenzoates from protected glycals
Saidhareddy, Puli,Ajay, Sama,Shaw, Arun K.
, p. 4407 - 4417 (2017/07/03)
Two efficient, metal free reagent systems, PhI(OAc)2-I2 (method A) and IBX-I2 (method B), for stereoselective synthesis of trans-2-deoxy-2-iodoglycosylacetates and O-iodobenzoates respectively from differently protected glycals have been developed. They are compatible with a variety of protecting groups and various functional groups at 2C-position. Hexose-3,2-enolone 8 is obtained directly from 2-acetoxy glycal 5 by method A. An application to modified method B has been shown by synthesis of a diastereomerically pure α-glycosyl ortho-hexynylbenzoate 12, a glycosyl donor from 3,4,6-tri-O-acetyl-D-glucal in two steps that has been further utilized in the synthesis of glycosides 13–18.
Reaction of organocuprate reagents with protected 1,2-anhydro sugars. Stereocontrolled synthesis of 2-deoxy-C-glycosyl compounds
Bellosta,Czernecki
, p. 275 - 284 (2007/10/02)
The reaction of protected 1,2-anhydro-α-D-gluco- and β-D-manno-pyranoses with alkyl and phenyl organocuprates afforded the corresponding C-glycosyl compounds in acceptable to high yield. Complete stereocontrol was obtained, leading respectively to the β-D or the α-D anomer. With the perbenzylated manno derivative, deoxygenation at C-2 was achieved in high yield, affording 2-deoxy-α-D-C-glycosyl compounds.
