2-Naphthylmethyl Protecting Group Strategyfor Streamlined Synthesis of a Fondaparinux Analogue
Abstract Fondaparinux synthesis remains challenging because of demanding stereochemical control, protecting group manipulation, and purification of highly functionalized intermediates. We report a 2-naphthylmethyl (Nap) protecting group strategy for an azide-functionalized fondaparinux analogue. Direct C-2 Nap installation, combined with C-6 2-(diphenylphosphinoyl)acetyl (DPPA)-assisted β-glucosylation, streamlined assembly, while Nap-mediated phase behavior enabled 17 of 20 intermediates to be isolated without chromatography. The final analogue showed anti-FXa activity comparable to commercial fondaparinux.
Authors
- Chengli Zong (ORCID: https://orcid.org/0000-0002-4749-0567)
- Xiao Liu (ORCID: https://orcid.org/0000-0001-6653-1582)
- Deqian Li
- Shiyan Mai
- Shuai Meng (ORCID: https://orcid.org/0000-0003-4196-6496)
- Tiantian Sun (ORCID: https://orcid.org/0009-0000-4734-6664)
- Yan Lin
- Huiting Li (ORCID: https://orcid.org/0000-0002-4215-8717)
- Zhenghao Wu
- Xiongyan Meng
- Min Li
Institutions
- Jiangnan University (CN)
- Shanghai Jiao Tong University (CN)
- Hainan University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-08-03
- DOI
- https://doi.org/10.1021/acs.orglett.6c02533
- Primary Topic
- Proteoglycans and glycosaminoglycans research
- Type
- article
- Field-Weighted Citation Impact
- 0.00