202919-82-2Relevant academic research and scientific papers
Practical synthesis of 2-deoxy sugars via metal free deiodination reactions
Yao, Wang,Wang, Hao,Zeng, Jing,Wan, Qian
, p. 454 - 478 (2022/01/20)
2-Deoxy-glycosides, in which the C-2 hydroxyl group is replaced with a hydrogen atom, are important motifs in numerous bioactive natural products and pharmaceutical molecules. Herein, an improved dilauroyl peroxide-mediated radical deiodination reaction b
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.
A simple, efficient alternative for highly stereoselective iodoacetoxylation of protected glycals
Gammon, David W.,Kinfe, Henok H.,De Vos, Dirk E.,Jacobs, Pierre A.,Sels, Bert F.
, p. 9533 - 9536 (2007/10/03)
Protected glycals are converted in high yields and selectivities in less than 2 h at low temperatures to 2-deoxy-2-iodoglycosyl acetates using the simple, inexpensive reagent mixture of ammonium iodide, hydrogen peroxide and acetic anhydride/acetic acid in acetonitrile. The corresponding 2-deoxy-2-bromoglycosyl acetates are obtained using ammonium bromide instead of the iodide, although longer reaction times are required and selectivities are inferior.
Stereoselective synthesis of 2-deoxy-beta-galactosides via 2-deoxy-2-bromo- and 2-deoxy-2-iodo-galactopyranosyl donors.
Durham, Timothy B,Roush, William R
, p. 1871 - 1874 (2007/10/03)
[reaction: see text] A series of 2-bromo- and 2-iodo-galactopyranosyl acetates and trichloroacetimidates were evaluated as glycosyl donors for the synthesis of 2-deoxygalactopyranosides. The best selectivity for the beta-glycosidic linkage was achieved by
Phosphonium salts of diacetoxyiodine(I) anions, new reagents for the iodoacetoxylation of alkenes
Kirschning, Andreas,Plumeier, Claus,Rose, Lars
, p. 33 - 34 (2007/10/03)
Novel phosphonium salts of diacetoxyiodine(I) anions 1 add to alkenes like tri-O-benzyl galactal 8 affording 1-acetoxy-2-iodopyranoses 12a,b which can efficiently be employed in the synthesis of 2-deoxyglycoside 14.
