5′-O-dimethoxytrityl-2′-O-terbutyldimethylsilyl-3′-O-succinyl pyridinium salt-2′,3',4',5',5''-pentadeuterium-β-D-ribofuranosyl-N⁴-benzoylcytidine

Base Information

• Chemical Name: 5′-O-dimethoxytrityl-2′-O-terbutyldimethylsilyl-3′-O-succinyl pyridinium salt-2′,3',4',5',5''-pentadeuterium-β-D-ribofuranosyl-N⁴-benzoylcytidine
• CAS No.: 1542260-47-8
• Molecular Formula: C₄₃H₄₉N₃O₈Si
• Molecular Weight: 768.923

Synonyms:5′-O-dimethoxytrityl-2′-O-terbutyldimethylsilyl-3′-O-succinyl pyridinium salt-2′,3',4',5',5''-pentadeuterium-β-D-ribofuranosyl-N⁴-benzoylcytidine

Chemical Property of 5′-O-dimethoxytrityl-2′-O-terbutyldimethylsilyl-3′-O-succinyl pyridinium salt-2′,3',4',5',5''-pentadeuterium-β-D-ribofuranosyl-N⁴-benzoylcytidine

Chemical Property:

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Technology Process of 5′-O-dimethoxytrityl-2′-O-terbutyldimethylsilyl-3′-O-succinyl pyridinium salt-2′,3',4',5',5''-pentadeuterium-β-D-ribofuranosyl-N⁴-benzoylcytidine

There total 9 articles about 5′-O-dimethoxytrityl-2′-O-terbutyldimethylsilyl-3′-O-succinyl pyridinium salt-2′,3',4',5',5''-pentadeuterium-β-D-ribofuranosyl-N⁴-benzoylcytidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.9%

5′-O-dimethoxytrityl-2′-O-tert-butyldimethylsilyl-3′-N,N-diisopropylcyanoethylphosphoramidite-2′,3′,4′,5′,5″-pentadeuterium-β-D-ribofuranosyl uridine (1542260-29-6) + tert-butyldimethylsilyl chloride (18162-48-6) → 5′-O-dimethoxytrityl-2′-O-terbutyldimethylsilyl-3′-O-succinyl pyridinium salt-2′,3',4',5',5''-pentadeuterium-β-D-ribofuranosyl-N4-benzoylcytidine (1542260-47-8) + 5'-O-dimethoxytrityl-3'-O-terbutyldimethylsilyl-2',3',5'-trihydroxy-2',3',4',5',5-pentadeuterium-β-D-ribofuranosyl-N4-benzoyl-cytidine (1542260-50-3)

Guidance literature:

With pyridine; silver nitrate; In tetrahydrofuran; at 20 ℃; for 2.5h;

Reference yield: 50.9%

5'-O-dimethoxytrityl-2',3',5'-trihydroxy-2',3',4',5',5-pentadeuterium-β-D-ribofuranosyl-N4-benzoyl-cytidine (1542260-44-5) + tert-butyldimethylsilyl chloride (18162-48-6) → 5′-O-dimethoxytrityl-2′-O-terbutyldimethylsilyl-3′-O-succinyl pyridinium salt-2′,3',4',5',5''-pentadeuterium-β-D-ribofuranosyl-N4-benzoylcytidine (1542260-47-8) + 5'-O-dimethoxytrityl-3'-O-terbutyldimethylsilyl-2',3',5'-trihydroxy-2',3',4',5',5-pentadeuterium-β-D-ribofuranosyl-N4-benzoyl-cytidine (1542260-50-3)

Guidance literature:

5'-O-dimethoxytrityl-2',3',5'-trihydroxy-2',3',4',5',5"-pentadeuterium-β-D-ribofuranosyl-N⁴-benzoyl-cytidine; With pyridine; silver nitrate; In tetrahydrofuran; at 20 ℃; for 0.166667h;

tert-butyldimethylsilyl chloride; In tetrahydrofuran; at 20 ℃; for 2.5h; Sealed tube;

Reference yield:

methyl ribofuranoside (1824-96-0,1824-97-1,3795-68-4,3795-69-5,4229-54-3,5531-18-0,7473-45-2,13039-63-9,13039-64-0,13039-65-1,13039-67-3,22416-73-5,22861-09-2,25129-51-5,52485-92-4,52689-55-1,52689-56-2,56607-40-0,72880-70-7,79083-42-4,86782-30-1,86782-31-2,89615-03-2,89673-67-6,89707-99-3,102045-32-9,135910-17-7) → 5′-O-dimethoxytrityl-2′-O-terbutyldimethylsilyl-3′-O-succinyl pyridinium salt-2′,3',4',5',5''-pentadeuterium-β-D-ribofuranosyl-N4-benzoylcytidine (1542260-47-8) + 5'-O-dimethoxytrityl-3'-O-terbutyldimethylsilyl-2',3',5'-trihydroxy-2',3',4',5',5-pentadeuterium-β-D-ribofuranosyl-N4-benzoyl-cytidine (1542260-50-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: water-d2 / 168 h / 110 °C / Inert atmosphere

2.1: pyridine / dichloromethane / 48 h / 0 - 4 °C / Sealed tube

3.1: hydrogen bromide / acetic acid / 0.5 h / 20 °C / Sealed tube

4.1: pyridine / chloroform / 72 h / 20 °C / Sealed tube

5.1: 1,1,1,3,3,3-hexamethyl-disilazane; ammonium sulfate / 15 h / Reflux

5.2: 0.25 h / 40 °C

5.3: 2.5 h / Reflux

6.1: sodium hydroxide; water; pyridine / methanol / 0.33 h / 0 °C

7.1: pyridine / 5 h / 0 °C

8.1: silver nitrate; pyridine / tetrahydrofuran / 0.17 h / 20 °C

8.2: 2.5 h / 20 °C / Sealed tube

With pyridine; ammonium sulfate; water; hydrogen bromide; water-d2; silver nitrate; 1,1,1,3,3,3-hexamethyl-disilazane; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetic acid;

upstream raw materials:

5′-O-dimethoxytrityl-2′-O-tert-butyldimethylsilyl-3′-N,N-diisopropylcyanoethylphosphoramidite-2′,3′,4′,5′,5″-pentadeuterium-β-D-ribofuranosyl uridine

tert-butyldimethylsilyl chloride

5'-O-dimethoxytrityl-2',3',5'-trihydroxy-2',3',4',5',5-pentadeuterium-β-D-ribofuranosyl-N⁴-benzoyl-cytidine

2′,3′,5′-tri-O-benzoyl-2′,3',4',5',5''-pentadeuterium-β-D-ribofuranosyl-N⁴-benzoylcytidine

Downstream raw materials:

5'-O-dimethoxytrityl-2'-O-terbutyldimethylsilyl-3'-N,N-diisopropyl-O-(2-cyanoethyl)phosphoramidite-2',3',5'-trihydroxy-2',3',4',5',5-pentadeuterium-β-D-ribofuranosyl-N⁴-benzoyl-cytidine

5'-O-dimethoxytrityl-2'-O-terbutyldimethylsilyl-3'-O-succinyl-pyridinium 2',3',5'-trihydroxy-2',3',4',5',5-pentadeuterium-β-D-ribofuranosyl-N⁴-benzoyl-cytidine

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