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

Base Information

Chemical Name:2-benzylthio-1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-5,6-dichloroindole
CAS No.:286949-73-3
Molecular Formula:C₃₇H₃₉Cl₂NO₅S₂Si
Molecular Weight:740.844
Hs Code.:

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

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

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

There total 8 articles about 2-benzylthio-1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-5,6-dichloroindole 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%

: 124-63-0
methanesulfonyl chloride

: 286949-71-1
2-benzylthio-1-(2-deoxy-5-O-tert-butyldiphenylsilyl-β-D-erythro-pentofuranosyl)-5,6-dichloroindole

: 286949-73-3
2-benzylthio-1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-5,6-dichloroindole

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

: 286949-73-3
2-benzylthio-1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-5,6-dichloroindole

Guidance literature:: Multi-step reaction with 8 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: 69 percent / P₂S₅ / tetrahydrofuran / 0.5 h / 20 °C

4.1: 98 percent / K₂CO₃ / acetone / 3.5 h / 20 °C

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

5.2: 92 percent / acetonitrile / 0.33 h

6.1: 91 percent / NaOMe / methanol / 2 h / 20 °C

7.1: 88 percent / pyridine / 24 h / 20 °C

8.1: 92 percent / pyridine / CH₂Cl₂ / 4.5 h / 20 °C

With pyridine; tetraphosphorus decasulfide; sulfuric acid; hydrogen; sodium methylate; sodium hydride; potassium carbonate; acetic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; dichloromethane; acetone; acetonitrile; 1.1: Esterification / 2.1: Reduction / 3.1: Substitution / 4.1: Benzylation / 5.1: Metallation / 5.2: Glycosylation / 6.1: Debenzoylation / 7.1: Silylation / 8.1: Mesylation;
DOI:10.1021/jm990320x

Reference yield:

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

: 286949-73-3
2-benzylthio-1-(2-deoxy-5-O-tert-butyldiphenylsilyl-3-O-mesyl-β-D-erythro-pentofuranosyl)-5,6-dichloroindole

Guidance literature:: Multi-step reaction with 7 steps

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

2.1: 69 percent / P₂S₅ / tetrahydrofuran / 0.5 h / 20 °C

3.1: 98 percent / K₂CO₃ / acetone / 3.5 h / 20 °C

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

4.2: 92 percent / acetonitrile / 0.33 h

5.1: 91 percent / NaOMe / methanol / 2 h / 20 °C

6.1: 88 percent / pyridine / 24 h / 20 °C

7.1: 92 percent / pyridine / CH₂Cl₂ / 4.5 h / 20 °C

With pyridine; tetraphosphorus decasulfide; hydrogen; sodium methylate; sodium hydride; potassium carbonate; acetic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; dichloromethane; acetone; acetonitrile; 1.1: Reduction / 2.1: Substitution / 3.1: Benzylation / 4.1: Metallation / 4.2: Glycosylation / 5.1: Debenzoylation / 6.1: Silylation / 7.1: Mesylation;
DOI:10.1021/jm990320x