1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-2,5,6-trichloroindole

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Chemical Name:1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-2,5,6-trichloroindole
CAS No.:286949-74-4
Molecular Formula:C₃₀H₃₂Cl₃NO₅SSi
Molecular Weight:653.098
Hs Code.:

Synonyms:1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-2,5,6-trichloroindole

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Chemical Property of 1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-2,5,6-trichloroindole

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Technology Process of 1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-2,5,6-trichloroindole

There total 7 articles about 1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-2,5,6-trichloroindole 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: 91.0%

: 124-63-0
methanesulfonyl chloride

: 286949-72-2
1-(2-deoxy-5-O-tert-butyldiphenylsilyl-β-D-erythro-pentofuranosyl)-2,5,6-trichloroindole

: 286949-74-4
1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-2,5,6-trichloroindole

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 4.5h;
DOI:10.1021/jm990320x

Reference yield:

: 37777-90-5
2-nitro-4,5-dichlorophenylacetic acid

: 286949-74-4
1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-2,5,6-trichloroindole

Guidance literature:: Multi-step reaction with 7 steps

1.1: 82 percent / concd H₂SO₄ / 7 h / Heating

2.1: 76 percent / H₂; AcOH / PtO₂ / 20 h / 20 °C / 2068.65 Torr

3.1: 70 percent / POCl₃; imidazole / 1,2-dichloro-ethane / 2.5 h / Heating

4.1: NaH / acetonitrile / 0.17 h / 20 °C

4.2: 92 percent / acetonitrile / 0.33 h

5.1: 98 percent / NaOMe / methanol / 2 h / 20 °C

6.1: 90 percent / pyridine / 24 h / 20 °C

7.1: 91 percent / pyridine / CH₂Cl₂ / 4.5 h / 20 °C

With pyridine; 1H-imidazole; sulfuric acid; hydrogen; sodium methylate; sodium hydride; acetic acid; trichlorophosphate; platinum(IV) oxide; In methanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile; 1.1: Esterification / 2.1: Reduction / 3.1: Chlorination / 4.1: Metallation / 4.2: Glycosylation / 5.1: Debenzoylation / 6.1: Silylation / 7.1: Mesylation;
DOI:10.1021/jm990320x

Reference yield:

: 286949-63-1
4,5-dichloro-2-nitrophenylacetic acid methyl ester

: 286949-74-4
1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-2,5,6-trichloroindole

Guidance literature:: Multi-step reaction with 6 steps

1.1: 76 percent / H₂; AcOH / PtO₂ / 20 h / 20 °C / 2068.65 Torr

2.1: 70 percent / POCl₃; imidazole / 1,2-dichloro-ethane / 2.5 h / Heating

3.1: NaH / acetonitrile / 0.17 h / 20 °C

3.2: 92 percent / acetonitrile / 0.33 h

4.1: 98 percent / NaOMe / methanol / 2 h / 20 °C

5.1: 90 percent / pyridine / 24 h / 20 °C

6.1: 91 percent / pyridine / CH₂Cl₂ / 4.5 h / 20 °C

With pyridine; 1H-imidazole; hydrogen; sodium methylate; sodium hydride; acetic acid; trichlorophosphate; platinum(IV) oxide; In methanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile; 1.1: Reduction / 2.1: Chlorination / 3.1: Metallation / 3.2: Glycosylation / 4.1: Debenzoylation / 5.1: Silylation / 6.1: Mesylation;
DOI:10.1021/jm990320x