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Logo of nihpaAbout Author manuscriptsSubmit a manuscriptHHS Public Access; Author Manuscript; Accepted for publication in peer reviewed journal;
 
From:
Angew Chem Int Ed Engl. Author manuscript; available in PMC 2013 July 9.
Published in final edited form as:
Angew Chem Int Ed Engl. 2012 July 9; 51(28): 6908–6911.
Published online 2012 June 11. doi: 10.1002/anie.201201690

Scheme 1

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Cyclic ntla cMO synthesis. a) allyl TMS, TiCl4, CH2Cl2, 98%; b) O3, MeOH; c) NaBH4, MeOH, 74% over 2 steps; d) TsCl, pyridine, 63%; e) methylamine, THF, 87%; f) methyl adipoyl chloride, DIPEA, CH2Cl2, 57%; g) 1,1′-carbonyl diimidazole, CH2Cl2; h) ethylenediamine, CH2Cl2; i) 2-chloroacetyl chloride, Et3N, CH2Cl2, 54% over 3 steps; j) LiOH, THF, H2O; k) N,N′-disuccinimidyl carbonate, pyridine, CH3CN, 68% over 2 steps; l) 5′-amine, 3′-alkyl disulfide ntla MO (21-, 23-, or 25-base), 0.1 M Na2B4O7 pH 8.5, DMSO, 69–95%; m) TCEP resin, 0.1 M Tris-HCl buffer, pH 8.4, 84–92%.

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  • Scheme 1
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