| Full text | |
| Author(s): |
Shamim, Anwar
[1]
;
Vasconcelos, Stanley N. S.
[2]
;
de Oliveira, Isadora Maria
[1]
;
Reis, Joel S.
[2]
;
Pimenta, Daniel C.
[3]
;
Zukerman-Schpector, Julio
[4]
;
Stefani, Helio A.
[2]
Total Authors: 7
|
| Affiliation: | [1] Univ Sao Paulo, Inst Quim, Av Prof Lineu Prestes 748, BR-05508000 Sao Paulo, SP - Brazil
[2] Univ Sao Paulo, Fac Ciencias Farmaceut, Av Prof Lineu Prestes 580, BR-0550800 Sao Paulo, SP - Brazil
[3] Inst Butantan, Sao Paulo, SP - Brazil
[4] Univ Fed Sao Carlos, Dept Quim, Sao Carlos, SP - Brazil
Total Affiliations: 4
|
| Document type: | Journal article |
| Source: | SYNTHESIS-STUTTGART; v. 49, n. 23, p. 5183-5196, DEC 2017. |
| Web of Science Citations: | 3 |
| Abstract | |
2,3-Unsaturated C-(triazolyl) glycosyl acetates have been synthesized from 3,4,6-tri-O-acetyl-D-glucal using C-glycosylation and click chemistry and were then used in a palladium-catalyzed Tsuji-Trost type allylic azidation reaction to afford the corresponding regioisomeric glucal-azide derivatives. Copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions with these glucal-based allylic azides using CuI as the catalyst, led to the corresponding glucal-based bis(triazole) derivatives. Performing further functional group modification and another click (CuAAC) reaction with each of these bis(triazolyl) glycosyl derivatives afforded tris(triazolyl) glycosyl derivatives. Two libraries of regioisomeric bis(triazole) derivatives and a small library of regioisomeric tris(triazole) derivatives of glucal were then synthesized using different alkynes. (AU) | |
| FAPESP's process: | 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions |
| Grantee: | Helio Alexandre Stefani |
| Support Opportunities: | Research Projects - Thematic Grants |