2,2-Dichloro-1,3-benzodioxole as a Hydroxyl Protection Reagent for Carbohydrate Compounds
The application of 2,2-dichloro-1,3-benzodioxole (DCBZ) as a versatile hydroxyl protection reagent in carbohydrate chemistry has been demonstrated. DCBZ exhibited high reactivity with diverse vicinal and remote dihydroxyl groups in furanoses and pyranoses to form benzodioxole (BZDO)-protected products. The BZDO group showed remarkable stability under basic, redox, and glycosylation conditions and can be efficiently removed under acid conditions in the presence of a diol, highlighting its utility in the orthogonal synthesis of complex glycans.
Authors
- Hanchao Cheng (ORCID: https://orcid.org/0000-0003-4905-5785)
- Henan Zhang (ORCID: https://orcid.org/0000-0002-5680-4687)
- Peixue Ling (ORCID: https://orcid.org/0000-0002-2783-7463)
- Junqiang Fang (ORCID: https://orcid.org/0000-0002-3973-1463)
- Changsheng Chen (ORCID: https://orcid.org/0000-0003-1627-2839)
- Shuang Li (ORCID: https://orcid.org/0000-0002-8522-8527)
- Lijun Zhang (ORCID: https://orcid.org/0000-0003-1946-7105)
Institutions
- Shandong University (CN)
- Shenzhen Polytechnic University (CN)
- The Polytechnic University of Japan (JP)
- Division of Undergraduate Education (US)
- GlycoScientific (United States) (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-06
- DOI
- https://doi.org/10.1021/acs.orglett.4c04838
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Key Technology Research and Development Program of Shandong
- Key Technologies Research and Development Program
- Shenzhen Science and Technology Innovation Program
- Basic and Applied Basic Research Foundation of Guangdong Province