Convenient synthesis of N-unprotected deoxynucleoside 3'-phosphoramidite building blocks by selective deacylation of N-acylated species and their facile conversion to other N-functionalized derivatives

Akihiro Ohkubo; Kazushi Sakamoto; Ken-ichi Miyata; Haruhiko Taguchi; Kohji Seio; Mitsuo Sekine

doi:10.1021/ol051949z

Convenient synthesis of N-unprotected deoxynucleoside 3'-phosphoramidite building blocks by selective deacylation of N-acylated species and their facile conversion to other N-functionalized derivatives

Org Lett. 2005 Nov 24;7(24):5389-92. doi: 10.1021/ol051949z.

Authors

Akihiro Ohkubo¹, Kazushi Sakamoto, Ken-ichi Miyata, Haruhiko Taguchi, Kohji Seio, Mitsuo Sekine

Affiliation

¹ Department of Life Science, Tokyo Institute of Technology, Nagatsuta, Midoriku, Yokohama 226-8501, Japan.

PMID: 16288513
DOI: 10.1021/ol051949z

Abstract

[reaction: see text] A new route to N-unprotected deoxynucleoside 3'-phosphoramidite building blocks by use of highly selective N-deacylation of commercially available N-acylated deoxynucleoside 3'-phosphoramidites is described. These compounds could be readily converted to other types of N-protected species by facile N-acylations with acylating reagents.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acylation
Catalysis
Molecular Structure
Oligodeoxyribonucleotides / chemical synthesis*
Oligodeoxyribonucleotides / chemistry
Organophosphorus Compounds / chemistry*

Substances

Oligodeoxyribonucleotides
Organophosphorus Compounds
phosphoramidite