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
Hs Code.:

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

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

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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%

: 124-63-0
methanesulfonyl chloride

: 58479-61-1
tert-butylchlorodiphenylsilane

: 801300-17-4
3-methyl-2,5,6-trichloro-1-(2-deoxy-β-D-ribofuranosyl)indole

: 801300-18-5
3-methyl-2,5,6-trichloro-1-(2-deoxy-3-O-methanesulfonyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)indole

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:

: 4330-21-6
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

: 801300-18-5
3-methyl-2,5,6-trichloro-1-(2-deoxy-3-O-methanesulfonyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)indole

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:

: 6725-44-6
methyl 2-(3,4-dichlorophenyl)acetate

: 801300-18-5
3-methyl-2,5,6-trichloro-1-(2-deoxy-3-O-methanesulfonyl-5-O-tert-butyldiphenylsilyl-β-D-ribofuranosyl)indole

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