𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Stereochemistry of the reaction of ribonucleoside cyclic 3′,5′-phosphorothioates with oxiranes

✍ Scribed by Andrzej Okruszek; Piotr Guga; Wojciech J. Stec

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
643 KB
Volume
2
Category
Article
ISSN
1042-7163

No coin nor oath required. For personal study only.

✦ Synopsis

The stereochemical course of the epoxide-induced oxidative rearrangement of ribonucleoside cyclic 3',5'phosphorothioates into the corresponding 2',3'-phosphates has been determined using styrene ['80] oxide and (Sp)-uridine cyclic 3',5'-phosphorothioate. The evidence of full stereoselectivity of this reaction is presented and mechanistic implications of the presence o f the nucleoside 2'-hydroxyl group are discussed in terms o f a classical Hamer Mechanism.

*To whom correspondence should be addressed. Dedicated to Professor Leopold Homer on the occasion of his eightieth birthday.

📜 SIMILAR VOLUMES

5-Butyl­thevinone: stereochemistry of th
5-Butyl­thevinone: stereochemistry of the Diels–Alder reaction of 5-butyl­thebaine with 3-buten-2-one
✍ Chen, Weibin ;Metcalf, Matthew D. ;Coop, Andrew ;Flippen-Anderson, Judith L. ;De 📂 Article 📅 2003 🏛 International Union of Crystallography 🌐 English ⚖ 216 KB

Single-crystal X-ray study T = 298 K Mean '(C±C) = 0.006 A Ê R factor = 0.056 wR factor = 0.124 Data-to-parameter ratio = 12.8 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.