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

Base Information

• Chemical Name: 1-[5-O-(4,4'-dimethoxytrityl)-2-O,2-C-propano-β-D-ribofuranosyl]thymine
• CAS No.: 664333-40-8
• Molecular Formula: C₃₄H₃₆N₂O₈
• Molecular Weight: 600.668
• Mol file: 664333-40-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 1-[5-O-(4,4'-dimethoxytrityl)-2-O,2-C-propano-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: 88.0%

1-[3-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-O,2-C-propano-β-D-ribofuranosyl]thymine (664333-39-5) → 1-[5-O-(4,4'-dimethoxytrityl)-2-O,2-C-propano-β-D-ribofuranosyl]thymine (664333-40-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1039/b306354b

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 1-[5-O-(4,4'-dimethoxytrityl)-2-O,2-C-propano-β-D-ribofuranosyl]thymine (664333-40-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 86 percent / pyridine / 12 h / 20 °C

2.1: 84 percent / imidazole / dimethylformamide / 12 h / 36 °C

3.1: BH₃ / various solvent(s); tetrahydrofuran / 12 h / 20 °C

3.2: 55 percent / aq. NaOH; H₂O₂ / various solvent(s); tetrahydrofuran / 2 h / 20 °C

4.1: 58 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

5.1: 87 percent / NaH / tetrahydrofuran / 2 h / 20 °C

6.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With pyridine; 1H-imidazole; borane; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b306354b

Reference yield:

1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose (157037-56-4) → 1-[5-O-(4,4'-dimethoxytrityl)-2-O,2-C-propano-β-D-ribofuranosyl]thymine (664333-40-8)

Guidance literature:

Multi-step reaction with 10 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: BH₃ / various solvent(s); tetrahydrofuran / 12 h / 20 °C

7.2: 55 percent / aq. NaOH; H₂O₂ / various solvent(s); tetrahydrofuran / 2 h / 20 °C

8.1: 58 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

9.1: 87 percent / NaH / tetrahydrofuran / 2 h / 20 °C

10.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With pyridine; 1H-imidazole; dmap; N,O-bis-(trimethylsilyl)-acetamide; cerium(III) chloride; borane; tetrabutyl ammonium fluoride; ammonia; sodium hydride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.2: Grignard addition;

DOI:10.1039/b306354b

upstream raw materials:

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

4,4'-dimethoxytrityl chloride

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

1-(2-C-allyl-β-D-ribofuranosyl)thymine