157
Views
0
CrossRef citations to date
0
Altmetric
Short Communication

Cyclopropylmethylidene as a versatile protecting group for carbohydrate synthesis

, , , &
Pages 294-308 | Received 08 Jan 2024, Accepted 13 Mar 2024, Published online: 23 Mar 2024

References

  • Vidal, S. Editor. Protecting Groups: Strategies and Applications in Carbohydrate Chemistry. John Wiley & Sons, Hoboken, New Jersey, 2019, 528. pp.
  • Fraser-Reid, B.; Wu, Z.; Udodong, U. E.; Ottosson, H. Armed/Disarmed Effects In Glycosyl Donors: Rationalization and Sidetracking. J. Org. Chem. 1990, 55, 6068–6070. DOI: 10.1021/jo00312a004.
  • Fraser-Reid, B.; Wu, Z.; Andrews, C. W.; Skowronski, E.; Bowen, J. P. Torsional Effects in Glycoside Reactivity: Saccharide Couplings Mediated By Acetal Protecting Groups J. Am. Chem. Soc. 1991, 113, 1434–1435. DOI: 10.1021/ja00004a066.
  • Dharuman, S.; Crich, D. Determination of the Influence of Side-Chain Conformation on Glycosylation Selectivity using Conformationally Restricted Donors. Chemistry. 2016, 22, 4535–4542. DOI: 10.1002/chem.201505019.
  • Bock, K.; Duus, J. O. A Conformational Study of Hydroxymethyl Groups in Carbohydrates Investigated by 1H NMR Spectroscopy. J. Carbohydr. Chem. 1994, 13, 513–543. DOI: 10.1080/07328309408011662.
  • Dey, S.; Jayaraman, N. Glycosidic Bond Hydrolysis in Septanosides: A Comparison Of Mono-, di-, and 2-chloro-2-deoxy-septanosides. Carbohydr. Res. 2014, 399, 49–56. DOI: 10.1016/j.carres.2014.05.013.
  • Nagata, W.; Okada, K.; Itazaki, H.; Uyeo, S. Synthetic Studies on Isoquinoline Alkaloids. II. Selective Conversion of 3, 9, 10-Substituted Tetrahydroprotoberberines into 3, 9, 10-Substituted 14-Deoxoprotopines. Total Synthesis of 3, 9, 10-Substituted 5, 6, 7, 8, 13, 14-Hexahydrodibenz (c, g) azecines. Chem. Pharm. Bull. 1975, 23, 2878–2890. DOI: 10.1248/cpb.23.2878.
  • Brady, S. F.; Hirschmann, R.; Veber, D. F. Some novel, acid-labile amine protecting groups. J. Org. Chem. 1977, 42, 143–146. DOI: 10.1021/jo00421a030.
  • Carpino, L. A.; Chao, H. G.; Ghassemi, S.; Mansour, E. M. E.; Riemer, C.; Warrass, R.; Sadat-Aalaee, D.; Truran, G. A.; Imazumi, H.; El-Faham, A.; Ionescu, D.; Ismail, M.; Kowaleski, T. L.; Han, C. H.; Wenschuh, H.; Beyermann, M.; Bienert, M.; Shroff, H.; Albericio, F.; Triolo, S. A.; Sole, N. A.; Kates, S. A. Novel Carboxylic Acid and Carboxamide Protective Groups Based on the Exceptional Stabilization of the Cyclopropylmethyl Cation. J. Org. Chem. 1995, 60, 7718–7719. DOI: 10.1021/jo00129a005.
  • Eichler, E.; Yan, F.; Sealy, J.; Whitfield, D. M. 1-Methyl 1′-Cyclopropylmethyl: An Acid Labile O-Protecting Group For Polymer-Supported Oligosaccharide Synthesis. Tetrahedron, 2001, 57, 6679–6693. DOI: 10.1016/S0040-4020(01)00582-8.
  • Kumar, A.; Saleeb, M.; Werz, D.; Elofsson, M. Cyclopropylmethyl Protection of Phenols: Total Synthesis of the Resveratrol Dimers Anigopreissin A and Resveratrol–Piceatannol Hybrid. ChemistryOpen, 2018, 7, 953–956. DOI: 10.1002/open.201800214.
  • Moumé-Pymbock, M.; Furukawa, T.; Mondal, S.; Crich, D. Probing the Influence of a 4,6-O-Acetal on the Reactivity of Galactopyranosyl Donors: Verification of the Disarming Influence of the trans-gauche Conformation of C5-C6 Bonds. J Am Chem Soc, 2013, 135, 14249–14255. DOI: 10.1021/ja405588x.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.