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. 2012 Apr 11;40(14):e108. doi: 10.1093/nar/gks303

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© 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.

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Scheme 4. — Synthesis of β-Cy3BdR phosphoramidite and α-Cy3BdR solid support. Reagents and conditions; (i) MeOH, 1% methanolic HCl, room temperature, 30 min; (ii) pyridine, p-toluoyl-chloride, 0°C then room temperature, 16 h; (iii) acetic acid, saturated HCl in acetic acid, acetyl chloride, 0°C then room temperature, 64% over three steps; (iv) THF, DCM, DMAP, 5-hexyn-1-ol, room temperature, 3.5 h, 53%; (v) methanolic ammonia, 45°C, 16 h, 82%; (vi) DMTCl, pyridine, DMAP, 1 h, room temperature, α 47%, β 41% (total 88%); (vii) 7, CuI, Pd(PPh₃)₄, Et₃N, DMF, 52 h, room temperature, α 66%, β 73%; (viii) 2-cyanoethyl-N,N-diisopropyl-chlorophosphoramidite, DIPEA, DCM, room temperature, 45 min, 94%; (ix) succinylated amino-link resin, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, DMAP, Et₃N.