Figure - PMC

Skip to main content

An official website of the United States government

Here's how you know

Here's how you know

Official websites use .gov
A .gov website belongs to an official government organization in the United States.

Secure .gov websites use HTTPS
A lock ( ) or https:// means you've safely connected to the .gov website. Share sensitive information only on official, secure websites.

View full-text article in PMC

. 2012 Sep 8;40(21):11126–11138. doi: 10.1093/nar/gks799

Search in PMC
Search in PubMed
View in NLM Catalog
Add to search

© The Author(s) 2012. Published by Oxford University Press.

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0), which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

PMC Copyright notice

Scheme 2. — Synthesis of 8-nitroguanosine nucleosides. Reagents and conditions: (i) Ac₂O (2.5 eq), Et₃N (2.6 eq), DMAP (0.1 eq), MeCN 0°C, r.t. 2 h (94%, 2b) (ii) Sat. bromine water (excess), H₂O, r.t. (90%, 3b) (iii) DMTCl (1.2 eq), pyridine, r.t., 6 h (94% 4a, 70% 4b); (iv) KNO₂ (10 eq), 18-C-6 (10 eq), DMF, 100°C, 6 h (36% 5a, 43% 5b); (v) TsOH (1.1 eq), CHCl₃, r.t. 1 h then 7 M NH₃ in MeOH, r.t., 48 h (73% 6a, 81% 6b); (vi) 7 M NH₃ in MeOH, r.t., 48 h (94%) (vii) DMTCl (1.2 eq), pyridine, r.t., 16 h (80%) (viii) DIPEA (12.5 eq), 2-cyanoethydiisopropylchlorophosphoramidite (1.2 eq), DCM, 0°C to r.t. 3 h (67%).