Issue 29, 2024

An efficient alternative to DBU in the oxathiaphospholane (OTP) method for the solid phase synthesis of P-stereodefined phosphorothioate analogs

Abstract

This study presents a modified (extended) 1,3,2-oxathiaphospholane (OTP) method for the synthesis of P-stereodefined phosphorothioate analogs in the presence of previously unused organic bases. TBD (5,7-triazabicyclo[4.4.0]dec-5-ene) and Verkade's proazaphosphatrane (2,8,9-trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane) are herein used for the first time as efficient organic bases compared to DBU, which is commonly used in the OTP approach.

Graphical abstract: An efficient alternative to DBU in the oxathiaphospholane (OTP) method for the solid phase synthesis of P-stereodefined phosphorothioate analogs

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Article information

Article type
Paper
Submitted
16 Apr 2024
Accepted
23 Jun 2024
First published
04 Jul 2024
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2024,14, 21174-21179

An efficient alternative to DBU in the oxathiaphospholane (OTP) method for the solid phase synthesis of P-stereodefined phosphorothioate analogs

K. Jastrzębska, RSC Adv., 2024, 14, 21174 DOI: 10.1039/D4RA02833C

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