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Synthesis of five-MemberedConformationally Locked 2´,4´-Carbocyclic ribo - Thimidine.

Synthesis of five-MemberedConformationally Locked 2´,4´-Carbocyclic ribo - Thimidine. Khobragade Premkumar Anandrao Chembiotek, Hinjewadi, Pune. Antisense therapeutic agent. 65%. 95%. Reagents and conditions: Acetone, sulphuric acid, rt, overnight.

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Synthesis of five-MemberedConformationally Locked 2´,4´-Carbocyclic ribo - Thimidine.

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  1. Synthesis of five-MemberedConformationally Locked 2´,4´-Carbocyclic ribo- Thimidine. Khobragade Premkumar Anandrao Chembiotek, Hinjewadi, Pune

  2. Antisense therapeutic agent.

  3. 65% 95% • Reagents and conditions: • Acetone, sulphuric acid, rt, overnight. • Oxalyl chloride, DMSO, ,-78°C, DIPEA, DCM .

  4. 75% 62% • Reagents and conditions: • Sodium Borohydride, EtOH, rt, 2 hr, • NaH, BnBr,-5°C to rt overnight.

  5. 65% • Reagents and conditions: • 80% AcOH, rt, overnight, • Sodium metaperiodate, THF, Water, rt, 4 hr.

  6. 63% 66% • Reagents and conditions: • NaOH, formalin,rt, overnight; • NaH, BnBr,-5°C to rt, 4 hr.

  7. 87% Reagents and conditions: (i) Oxalyl chloride, DMSO,-78°C, DIPEA, DCM, (ii) PPh3+CH3Br-, 1.6 M butyllithiumin hexane, THF, -78 °C to rt overnight.

  8. 95% 70% Reagents and conditions:80% (i) 9-BBN, THF, 3 N NaOH, 33% H2O2, (ii) Oxalyl chloride, DMSO, -78 °C, DIPEA, DCM, PPh 3+CH3Br-, 1.6 M butyllithium in hexane, THF, -78 °C to rt overnight.

  9. 80% • Reagents and conditions: • Acetic acid, acetic anhydride, triflic acid, rt, 30 min. • persilylated thymine, TMSOTf, CH3CN, 0 °C to rt, overnight.

  10. 72% • Reagents and conditions: • 27% methanolic NH3,rt, overnight, • DMAP, phenyl chlorothionoformate, pyridine,rt, overnight.

  11. 73% 76% • Reagents and conditions: • Bu3SnH, toluene, AIBN, 4 h, • 20% Pd(OH)2/ C, Ammonium Formate, Methanol, Reflux, 8 h.

  12. 74% 80% • Reagents and conditions: • DMTr-Cl, Pyridine, Overnight, • 2-cyanoethyl N,N-diisopropylphosphoramidochloridite, DIPEA, dry THF, overnight.

  13. Thank you.

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