Issue 24, 2010

Stereoselective formation of a P–P bond in the reaction of 2-alkoxy-2-thio-1,3,2-oxathiaphospholanes with O,O-dialkyl H-phosphonates and H-thiophosphonates

Abstract

A new method for the formation of organohypophosphates containing a P–P bond under mild conditions, based on the DBU-assisted reaction of 2-alkoxy-2-thio-1,3,2-oxathiaphospholanes with O,O-dialkyl H-phosphonates or H-thiophosphonates, has been elaborated. The resulting triesters of P1-thio- and P1,P2-dithiohypophosphoric acids, respectively, having O-methyl or O-ethyl groups, can be selectively dealkylated to form the corresponding di- or monoesters. Appropriately protected 2′-deoxyguanosine-3′-O-(2-thio-1,3,2-oxathiaphospholane) was converted into the corresponding P1-thio- and P1,P2-dithiohypophosphate esters in a highly stereoselective manner (98%+ and 90%+, respectively).

Graphical abstract: Stereoselective formation of a P–P bond in the reaction of 2-alkoxy-2-thio-1,3,2-oxathiaphospholanes with O,O-dialkyl H-phosphonates and H-thiophosphonates

Supplementary files

Article information

Article type
Paper
Submitted
10 May 2010
Accepted
26 Aug 2010
First published
14 Oct 2010

Org. Biomol. Chem., 2010,8, 5505-5510

Stereoselective formation of a P–P bond in the reaction of 2-alkoxy-2-thio-1,3,2-oxathiaphospholanes with O,O-dialkyl H-phosphonates and H-thiophosphonates

D. Błaziak, P. Guga, A. Jagiełło, D. Korczyński, A. Maciaszek, A. Nowicka, A. Pietkiewicz and W. J. Stec, Org. Biomol. Chem., 2010, 8, 5505 DOI: 10.1039/C0OB00104J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements