Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst
Нема приказа
Аутори
Stevanović, Dragana D.Pejović, Anka
Damljanović, Ivan S.
Minić, Aleksandra
Bogdanović, Goran A.
Vukićević, Mirjana
Radulović, Niko S.
Vukićević, Rastko D.
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
In situ generated zirconium catalyst from a sacrificial zirconium anode was successfully applied to promote Ferrier rearrangement of 3,4,5-tri-O-acetyl-D-glucal and 6-deoxy-3,4-di-O-acetyl-L-glucal (3,4-di- O-acetyl-L-rhamnal) in the presence of three thiols and eleven thiophenols as nucleophiles. A simple constant current electrolysis (20 mA, 0.4 F mol(-1)) of an acetonitrile solution of lithium perchlorate (0.1 M) containing the corresponding glycal and S-nucleophiles, using a zirconium anode and a platinum cathode resulted in the successful synthesis of the corresponding 2,3-unsaturated peracetylated thioglycosides (with an average anomer ratio alpha/beta-4.129 in the case of peracetylated D-glucal and 8.740 in the case of L-rhamnal). The same procedure proved to be appropriate in synthesizing dihydropyran derivatives (C-glycosides) using allyltrimethylsilane as the nucleophile (only alpha-anomers were obtained). All new compounds were fully characterized by spectral data, whereas s...ingle-crystal X-ray analysis was performed for two thioglycosides. (C) 2015 Elsevier Ltd. All rights reserved.
Кључне речи:
Peracetylated D-glucal / Peracetylated L-rhamnal / Thiophenols / Pseudoglycals / Anodic generation of catalyst / ZirconiumИзвор:
Carbohydrate Research, 2015, 407, 111-121Финансирање / пројекти:
- Нове електрохемијске и хемијске методе у синтези органских једињења од интереса за медицину и хемију материјала (RS-MESTD-Basic Research (BR or ON)-172034)
DOI: 10.1016/j.carres.2015.02.001
ISSN: 0008-6215; 1873-426X
PubMed: 25746956
WoS: 000352217900016
Scopus: 2-s2.0-84923858552
Колекције
Институција/група
VinčaTY - JOUR AU - Stevanović, Dragana D. AU - Pejović, Anka AU - Damljanović, Ivan S. AU - Minić, Aleksandra AU - Bogdanović, Goran A. AU - Vukićević, Mirjana AU - Radulović, Niko S. AU - Vukićević, Rastko D. PY - 2015 UR - https://vinar.vin.bg.ac.rs/handle/123456789/489 AB - In situ generated zirconium catalyst from a sacrificial zirconium anode was successfully applied to promote Ferrier rearrangement of 3,4,5-tri-O-acetyl-D-glucal and 6-deoxy-3,4-di-O-acetyl-L-glucal (3,4-di- O-acetyl-L-rhamnal) in the presence of three thiols and eleven thiophenols as nucleophiles. A simple constant current electrolysis (20 mA, 0.4 F mol(-1)) of an acetonitrile solution of lithium perchlorate (0.1 M) containing the corresponding glycal and S-nucleophiles, using a zirconium anode and a platinum cathode resulted in the successful synthesis of the corresponding 2,3-unsaturated peracetylated thioglycosides (with an average anomer ratio alpha/beta-4.129 in the case of peracetylated D-glucal and 8.740 in the case of L-rhamnal). The same procedure proved to be appropriate in synthesizing dihydropyran derivatives (C-glycosides) using allyltrimethylsilane as the nucleophile (only alpha-anomers were obtained). All new compounds were fully characterized by spectral data, whereas single-crystal X-ray analysis was performed for two thioglycosides. (C) 2015 Elsevier Ltd. All rights reserved. T2 - Carbohydrate Research T1 - Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst VL - 407 SP - 111 EP - 121 DO - 10.1016/j.carres.2015.02.001 ER -
@article{ author = "Stevanović, Dragana D. and Pejović, Anka and Damljanović, Ivan S. and Minić, Aleksandra and Bogdanović, Goran A. and Vukićević, Mirjana and Radulović, Niko S. and Vukićević, Rastko D.", year = "2015", abstract = "In situ generated zirconium catalyst from a sacrificial zirconium anode was successfully applied to promote Ferrier rearrangement of 3,4,5-tri-O-acetyl-D-glucal and 6-deoxy-3,4-di-O-acetyl-L-glucal (3,4-di- O-acetyl-L-rhamnal) in the presence of three thiols and eleven thiophenols as nucleophiles. A simple constant current electrolysis (20 mA, 0.4 F mol(-1)) of an acetonitrile solution of lithium perchlorate (0.1 M) containing the corresponding glycal and S-nucleophiles, using a zirconium anode and a platinum cathode resulted in the successful synthesis of the corresponding 2,3-unsaturated peracetylated thioglycosides (with an average anomer ratio alpha/beta-4.129 in the case of peracetylated D-glucal and 8.740 in the case of L-rhamnal). The same procedure proved to be appropriate in synthesizing dihydropyran derivatives (C-glycosides) using allyltrimethylsilane as the nucleophile (only alpha-anomers were obtained). All new compounds were fully characterized by spectral data, whereas single-crystal X-ray analysis was performed for two thioglycosides. (C) 2015 Elsevier Ltd. All rights reserved.", journal = "Carbohydrate Research", title = "Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst", volume = "407", pages = "111-121", doi = "10.1016/j.carres.2015.02.001" }
Stevanović, D. D., Pejović, A., Damljanović, I. S., Minić, A., Bogdanović, G. A., Vukićević, M., Radulović, N. S.,& Vukićević, R. D.. (2015). Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst. in Carbohydrate Research, 407, 111-121. https://doi.org/10.1016/j.carres.2015.02.001
Stevanović DD, Pejović A, Damljanović IS, Minić A, Bogdanović GA, Vukićević M, Radulović NS, Vukićević RD. Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst. in Carbohydrate Research. 2015;407:111-121. doi:10.1016/j.carres.2015.02.001 .
Stevanović, Dragana D., Pejović, Anka, Damljanović, Ivan S., Minić, Aleksandra, Bogdanović, Goran A., Vukićević, Mirjana, Radulović, Niko S., Vukićević, Rastko D., "Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst" in Carbohydrate Research, 407 (2015):111-121, https://doi.org/10.1016/j.carres.2015.02.001 . .