Stepwise PEG synthesis featuring deprotection and coupling in one pot
The stepwise synthesis of monodisperse polyethylene glycols (PEGs) and their derivatives usually involves using an acid-labile protecting group such as DMTr and coupling the two PEG moieties together under basic Williamson ether formation conditions. Using this approach, each elongation of PEG is ac...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2021-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.17.207 |
| _version_ | 1831703650892775424 |
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| author | Logan Mikesell Dhananjani N. A. M. Eriyagama Yipeng Yin Bao-Yuan Lu Shiyue Fang |
| author_facet | Logan Mikesell Dhananjani N. A. M. Eriyagama Yipeng Yin Bao-Yuan Lu Shiyue Fang |
| author_sort | Logan Mikesell |
| collection | DOAJ |
| description | The stepwise synthesis of monodisperse polyethylene glycols (PEGs) and their derivatives usually involves using an acid-labile protecting group such as DMTr and coupling the two PEG moieties together under basic Williamson ether formation conditions. Using this approach, each elongation of PEG is achieved in three steps – deprotection, deprotonation and coupling – in two pots. Here, we report a more convenient approach for PEG synthesis featuring the use of a base-labile protecting group such as the phenethyl group. Using this approach, each elongation of PEG can be achieved in two steps – deprotection and coupling – in only one pot. The deprotonation step, and the isolation and purification of the intermediate product after deprotection using existing approaches are no longer needed when the one-pot approach is used. Because the stepwise PEG synthesis usually requires multiple PEG elongation cycles, the new PEG synthesis method is expected to significantly lower PEG synthesis cost. |
| first_indexed | 2024-12-20T15:44:25Z |
| format | Article |
| id | doaj.art-6126e44e1cf0488f96c9d684d7eb5f8b |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T15:44:25Z |
| publishDate | 2021-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-6126e44e1cf0488f96c9d684d7eb5f8b2022-12-21T19:35:02ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-12-011712976298210.3762/bjoc.17.2071860-5397-17-207Stepwise PEG synthesis featuring deprotection and coupling in one potLogan Mikesell0Dhananjani N. A. M. Eriyagama1Yipeng Yin2Bao-Yuan Lu3Shiyue Fang4Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USADepartment of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USADepartment of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USAChampionX, 11177 South Stadium Drive, Sugar Land, TX 77478, USADepartment of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USAThe stepwise synthesis of monodisperse polyethylene glycols (PEGs) and their derivatives usually involves using an acid-labile protecting group such as DMTr and coupling the two PEG moieties together under basic Williamson ether formation conditions. Using this approach, each elongation of PEG is achieved in three steps – deprotection, deprotonation and coupling – in two pots. Here, we report a more convenient approach for PEG synthesis featuring the use of a base-labile protecting group such as the phenethyl group. Using this approach, each elongation of PEG can be achieved in two steps – deprotection and coupling – in only one pot. The deprotonation step, and the isolation and purification of the intermediate product after deprotection using existing approaches are no longer needed when the one-pot approach is used. Because the stepwise PEG synthesis usually requires multiple PEG elongation cycles, the new PEG synthesis method is expected to significantly lower PEG synthesis cost.https://doi.org/10.3762/bjoc.17.207base-labilemonodispersepegpolyethylene glycolprotecting group |
| spellingShingle | Logan Mikesell Dhananjani N. A. M. Eriyagama Yipeng Yin Bao-Yuan Lu Shiyue Fang Stepwise PEG synthesis featuring deprotection and coupling in one pot Beilstein Journal of Organic Chemistry base-labile monodisperse peg polyethylene glycol protecting group |
| title | Stepwise PEG synthesis featuring deprotection and coupling in one pot |
| title_full | Stepwise PEG synthesis featuring deprotection and coupling in one pot |
| title_fullStr | Stepwise PEG synthesis featuring deprotection and coupling in one pot |
| title_full_unstemmed | Stepwise PEG synthesis featuring deprotection and coupling in one pot |
| title_short | Stepwise PEG synthesis featuring deprotection and coupling in one pot |
| title_sort | stepwise peg synthesis featuring deprotection and coupling in one pot |
| topic | base-labile monodisperse peg polyethylene glycol protecting group |
| url | https://doi.org/10.3762/bjoc.17.207 |
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