3-methyl-2,5,6-trichloro-1-(2-deoxy-3-O-methanesulfonyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)indole

Base Information

• Chemical Name: 3-methyl-2,5,6-trichloro-1-(2-deoxy-3-O-methanesulfonyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)indole
• CAS No.: 801300-18-5
• Molecular Formula: C₃₁H₃₄Cl₃NO₅SSi
• Molecular Weight: 667.125
• Mol file: 801300-18-5.mol

Synonyms:3-methyl-2,5,6-trichloro-1-(2-deoxy-3-O-methanesulfonyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)indole

Chemical Property of 3-methyl-2,5,6-trichloro-1-(2-deoxy-3-O-methanesulfonyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-methyl-2,5,6-trichloro-1-(2-deoxy-3-O-methanesulfonyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)indole

There total 8 articles about 3-methyl-2,5,6-trichloro-1-(2-deoxy-3-O-methanesulfonyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)indole 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: 63.0%

methanesulfonyl chloride (124-63-0) + tert-butylchlorodiphenylsilane (58479-61-1) + 3-methyl-2,5,6-trichloro-1-(2-deoxy-β-D-ribofuranosyl)indole (801300-17-4) → 3-methyl-2,5,6-trichloro-1-(2-deoxy-3-O-methanesulfonyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)indole (801300-18-5)

Guidance literature:

tert-butylchlorodiphenylsilane; 3-methyl-2,5,6-trichloro-1-(2-deoxy-β-D-ribofuranosyl)indole; With pyridine; at 20 ℃; for 16h;

methanesulfonyl chloride; With pyridine; at 20 ℃; for 4h;

DOI:10.1021/jm0400146

Reference yield:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → 3-methyl-2,5,6-trichloro-1-(2-deoxy-3-O-methanesulfonyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)indole (801300-18-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 0.25 h / 20 - 25 °C

1.2: 84 percent / tetrahydrofuran; toluene / 3 h / 20 °C

2.1: 57 percent / NaOMe / methanol / 2 h / 20 °C

3.1: pyridine / 16 h / 20 °C

3.2: 63 percent / pyridine / 4 h / 20 °C

With pyridine; sodium methylate; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1021/jm0400146

Reference yield:

methyl 2-(3,4-dichlorophenyl)acetate (6725-44-6) → 3-methyl-2,5,6-trichloro-1-(2-deoxy-3-O-methanesulfonyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)indole (801300-18-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaNH₂; NH₃ / tetrahydrofuran / 0.5 h / -78 °C

1.2: 89 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: 98 percent / H₂SO₄; aq. HNO₃ / 0.33 h / 0 °C

3.1: 3.72 g / AcOH / 2 h / 20 °C

4.1: POCl₃ / acetonitrile / 1 h / Heating

4.2: 39 percent / imidazole / acetonitrile / 16 h / Heating

5.1: NaH / tetrahydrofuran / 0.25 h / 20 - 25 °C

5.2: 84 percent / tetrahydrofuran; toluene / 3 h / 20 °C

6.1: 57 percent / NaOMe / methanol / 2 h / 20 °C

7.1: pyridine / 16 h / 20 °C

7.2: 63 percent / pyridine / 4 h / 20 °C

With pyridine; sulfuric acid; ammonia; nitric acid; sodium methylate; sodium hydride; sodium amide; acetic acid; trichlorophosphate; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/jm0400146

upstream raw materials:

methanesulfonyl chloride

tert-butylchlorodiphenylsilane

3-methyl-2,5,6-trichloro-1-(2-deoxy-β-D-ribofuranosyl)indole

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