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
| Autor: | Sama Ajay, Puli Saidhareddy, Arun K. Shaw |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Iodosobenzene
chemistry.chemical_classification Glycal 010405 organic chemistry Iodobenzoates Organic Chemistry Glycoside chemistry.chemical_element 010402 general chemistry Iodine 01 natural sciences Biochemistry 0104 chemical sciences chemistry.chemical_compound chemistry Reagent Drug Discovery Organic chemistry Stereoselectivity Glycosyl donor |
| Zdroj: | Tetrahedron. 73:4407-4417 |
| ISSN: | 0040-4020 |
| Popis: | Two efficient, metal free reagent systems, PhI(OAc) 2 -I 2 (method A) and IBX-I 2 (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 2 C -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 . |
| Databáze: | OpenAIRE |
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