1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-methanesulfonyloxyethyl)-β-D-ribofuranosyl]thymine

Base Information

• Chemical Name: 1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-methanesulfonyloxyethyl)-β-D-ribofuranosyl]thymine
• CAS No.: 664333-43-1
• Molecular Formula: C₄₀H₅₂N₂O₁₁SSi
• Molecular Weight: 797.011
• Mol file: 664333-43-1.mol

Synonyms:1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-methanesulfonyloxyethyl)-β-D-ribofuranosyl]thymine

Chemical Property of 1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-methanesulfonyloxyethyl)-β-D-ribofuranosyl]thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-methanesulfonyloxyethyl)-β-D-ribofuranosyl]thymine

There total 10 articles about 1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-methanesulfonyloxyethyl)-β-D-ribofuranosyl]thymine 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: 83.0%

methanesulfonyl chloride (124-63-0) + 1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-hydroxyethyl)-β-D-ribofuranosyl]thymine (664333-42-0) → 1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-methanesulfonyloxyethyl)-β-D-ribofuranosyl]thymine (664333-43-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1039/b306354b

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-methanesulfonyloxyethyl)-β-D-ribofuranosyl]thymine (664333-43-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / pyridine / 12 h / 20 °C

2: 84 percent / imidazole / dimethylformamide / 12 h / 36 °C

3: aq. NaIO₄; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 20 °C

4: 608 mg / NaBH₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

5: 83 percent / DMAP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1039/b306354b

Reference yield:

1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose (157037-56-4) → 1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-methanesulfonyloxyethyl)-β-D-ribofuranosyl]thymine (664333-43-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: CeCl₃*7H₂O / tetrahydrofuran; diethyl ether / 2 h / -78 °C

1.2: tetrahydrofuran; diethyl ether / 2 h / -78 °C

2.1: 3.35 g / DMAP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

3.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / Heating

3.2: SnCl₄ / acetonitrile / 3 h / Heating

4.1: 3.71 g / ammonia / methanol / 48 h / 20 °C

5.1: 86 percent / pyridine / 12 h / 20 °C

6.1: 84 percent / imidazole / dimethylformamide / 12 h / 36 °C

7.1: aq. NaIO₄; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 20 °C

8.1: 608 mg / NaBH₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

9.1: 83 percent / DMAP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N,O-bis-(trimethylsilyl)-acetamide; cerium(III) chloride; ammonia; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.2: Grignard addition;

DOI:10.1039/b306354b

upstream raw materials:

methanesulfonyl chloride

1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-C-(2-hydroxyethyl)-β-D-ribofuranosyl]thymine

4,4'-dimethoxytrityl chloride

1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose

Downstream raw materials:

1-[5-O-(4,4'-dimethoxytrityl)-2-O,2-C-ethano-β-D-ribofuranosyl]thymine

1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-O,2-C-ethano-β-D-ribofuranosyl]thymine