1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoroindole

Base Information

• Chemical Name: 1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoroindole
• CAS No.: 867176-94-1
• Molecular Formula: C₂₉H₂₆FNO₅
• Molecular Weight: 487.528
• Mol file: 867176-94-1.mol

Synonyms:1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoroindole

Chemical Property of 1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoroindole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoroindole

There total 1 articles about 1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoroindole 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: 92.0%

5-fluoro-1H-indole (399-52-0) + 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → 1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoroindole (867176-94-1)

Guidance literature:

With sodium hydride; In acetonitrile; at 20 ℃; for 0.333333h;

DOI:10.1139/V07-020

Reference yield:

1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoroindole (867176-94-1) → 1-(2'-deoxy-5'-O-tert-butyldiphenylsilyl-3'-O-mesyl-β-D-erythro-pentofuranosyl)-5-fluoroindole (943524-19-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / MeONa; methanol / 2 h / 20 °C

2: 86 percent / pyridine / 24 h / 20 °C

3: 89 percent / pyridine / CH₂Cl₂ / 4.5 h / 20 °C

With pyridine; methanol; sodium methylate; In dichloromethane;

DOI:10.1139/V07-020

Reference yield:

1-[2'-deoxy-3',5'-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoroindole (867176-94-1) → 1-[3-O-(P-β-cyanoethyl-N,N-diisopropylaminophosphinyl)-5-(4,4'-dimethoxytrityl)-2-deoxy-β-D-ribofuranosyl]-5-fluoroindole

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / pyridine / 20 °C

2: 79 percent / iPr₂NEt / CH₂Cl₂ / 1 h / 20 °C

With pyridine; N-ethyl-N,N-diisopropylamine; In dichloromethane; 1: Substitution / 2: Substitution;

DOI:10.1080/07328319908044634

upstream raw materials:

5-fluoro-1H-indole

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Downstream raw materials:

1-(2'-deoxy-5'-O-tert-butyldiphenylsilyl-β-D-erythro-pentofuranosyl)-5-fluoroindole

1-(2'-deoxy-5'-O-tert-butyldiphenylsilyl-3'-O-mesyl-β-D-erythro-pentofuranosyl)-5-fluoroindole

1-[5-(4,4'-dimethoxytrityl)-2-deoxy-β-D-ribofuranosyl]-5-fluoroindole