Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction
An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently acce...
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| Format: | Article |
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MDPI AG
2017-01-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/22/1/84 |
| _version_ | 1818276445490774016 |
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| author | Chengyuan Liang Weihui Ju Shunjun Ding Han Sun Gennian Mao |
| author_facet | Chengyuan Liang Weihui Ju Shunjun Ding Han Sun Gennian Mao |
| author_sort | Chengyuan Liang |
| collection | DOAJ |
| description | An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently accepted mechanism advanced by Vorbrueggen has been proposed and verified by experiments. In practice, this catalyst-free method provides easy access to Capecitabine in high yield. |
| first_indexed | 2024-12-12T22:45:46Z |
| format | Article |
| id | doaj.art-ae8f445d165842589c88ed5d3469e7ca |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-12T22:45:46Z |
| publishDate | 2017-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-ae8f445d165842589c88ed5d3469e7ca2022-12-22T00:09:12ZengMDPI AGMolecules1420-30492017-01-012218410.3390/molecules22010084molecules22010084Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson ReactionChengyuan Liang0Weihui Ju1Shunjun Ding2Han Sun3Gennian Mao4Faculty of Pharmacy, Shaanxi University of Science & Technology, 6 Xuefu Road, Xi’an 710021, ChinaFaculty of Pharmacy, Shaanxi University of Science & Technology, 6 Xuefu Road, Xi’an 710021, ChinaFaculty of Pharmacy, Shaanxi University of Science & Technology, 6 Xuefu Road, Xi’an 710021, ChinaFaculty of Pharmacy, Shaanxi University of Science & Technology, 6 Xuefu Road, Xi’an 710021, ChinaFaculty of Pharmacy, Shaanxi University of Science & Technology, 6 Xuefu Road, Xi’an 710021, ChinaAn effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently accepted mechanism advanced by Vorbrueggen has been proposed and verified by experiments. In practice, this catalyst-free method provides easy access to Capecitabine in high yield.http://www.mdpi.com/1420-3049/22/1/84nucleosidesglycosyl chioridesN-glycosylationcatalyst free reactionsilyl-Hilbert-Johnson reaction |
| spellingShingle | Chengyuan Liang Weihui Ju Shunjun Ding Han Sun Gennian Mao Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction Molecules nucleosides glycosyl chiorides N-glycosylation catalyst free reaction silyl-Hilbert-Johnson reaction |
| title | Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction |
| title_full | Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction |
| title_fullStr | Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction |
| title_full_unstemmed | Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction |
| title_short | Effective Synthesis of Nucleosides Utilizing O-Acetyl-Glycosyl Chlorides as Glycosyl Donors in the Absence of Catalyst: Mechanism Revision and Application to Silyl-Hilbert-Johnson Reaction |
| title_sort | effective synthesis of nucleosides utilizing o acetyl glycosyl chlorides as glycosyl donors in the absence of catalyst mechanism revision and application to silyl hilbert johnson reaction |
| topic | nucleosides glycosyl chiorides N-glycosylation catalyst free reaction silyl-Hilbert-Johnson reaction |
| url | http://www.mdpi.com/1420-3049/22/1/84 |
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