𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Total Synthesis of Everninomicin 13,384-1—Part 4: Explorations of Methodology; Stereocontrolled Synthesis of 1,1′-Disaccharides, 1,2-Seleno Migrations in Carbohydrates, and Solution- and Solid-Phase Synthesis of 2-Deoxy Glycosides and Orthoesters

✍ Scribed by K. C. Nicolaou; Konstantina C. Fylaktakidou; Helen J. Mitchell; Floris L. van Delft; Rosa Maria Rodríguez; Scott R. Conley; Zhendong Jin

Book ID
102679179
Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
609 KB
Volume
6
Category
Article
ISSN
0947-6539

No coin nor oath required. For personal study only.

✦ Synopsis

Methods for the stereocontrolled construction of 1,1'-disaccharides, 2-deoxy glycosides, and orthoesters are reported. Specifically, a tin-acetal moiety was utilized to fix the anomeric stereochemistry of a carbohydrate acceptor leading to an efficient and stereoselective synthesis of 1,1'-disaccharides, while a newly discovered 1,2-phenylseleno migration reaction in carbohydrates opened entries to 2-deoxy glycosides and orthoesters. Thus, reaction of 2-hydroxy phenylselenoglycosides with DAST led to 2-phenylselenoglycosyl fluorides which reacted with carbohydrate acceptors to afford, stereoselectively, 2-phenylselenoglycosides. The latter compounds could be reductively deselenated to 2-deoxy glycosides or oxidatively converted to orthoesters via the corresponding ketene acetals.

📜 SIMILAR VOLUMES

1,2-Seleno Migrations in Carbohydrate Ch
1,2-Seleno Migrations in Carbohydrate Chemistry: Solution and Solid-Phase Synthesis of 2-Deoxy Glycosides, Orthoesters, and Allyl Orthoesters
✍ K. C. Nicolaou; Helen J. Mitchell; Konstantina C. Fylaktakidou; Hideo Suzuki; Ro 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 290 KB 👁 2 views

We thank Drs. D. H. Huang and G. Siuzdak for NMR spectroscopic and mass spectrometric assistance, respectively. We gratefully thank Nicolas Winssinger for helpful discussions and preparation of the selenium bromide resin.

1,2-Seleno Migrations in Carbohydrate Ch
1,2-Seleno Migrations in Carbohydrate Chemistry: Solution and Solid-Phase Synthesis of 2-Deoxy Glycosides, Orthoesters, and Allyl Orthoesters
✍ K. C. Nicolaou; Helen J. Mitchell; Konstantina C. Fylaktakidou; Hideo Suzuki; Ro 📂 Article 📅 2000 🏛 John Wiley and Sons 🌐 English ⚖ 290 KB 👁 2 views

We thank Drs. D. H. Huang and G. Siuzdak for NMR spectroscopic and mass spectrometric assistance, respectively. We gratefully thank Nicolas Winssinger for helpful discussions and preparation of the selenium bromide resin.