2-benzylthio-1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5,6-dichloroindole

Base Information

Chemical Name:2-benzylthio-1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5,6-dichloroindole
CAS No.:286949-67-5
Molecular Formula:C₃₆H₃₁Cl₂NO₅S
Molecular Weight:660.618
Hs Code.:

Synonyms:2-benzylthio-1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5,6-dichloroindole

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Chemical Property of 2-benzylthio-1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5,6-dichloroindole

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Technology Process of 2-benzylthio-1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5,6-dichloroindole

There total 5 articles about 2-benzylthio-1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-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%

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

: 286949-64-2
2-benzylthio-5,6-dichloroindole

: 286949-67-5
2-benzylthio-1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5,6-dichloroindole

Guidance literature:: 2-benzylthio-5,6-dichloroindole; With sodium hydride; In acetonitrile; at 20 ℃; for 0.166667h;

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride; In acetonitrile; for 0.333333h; Further stages.;
DOI:10.1021/jm990320x

Reference yield:

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

: 286949-67-5
2-benzylthio-1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5,6-dichloroindole

Guidance literature:: Multi-step reaction with 5 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

With tetraphosphorus decasulfide; sulfuric acid; hydrogen; sodium hydride; potassium carbonate; acetic acid; platinum(IV) oxide; In tetrahydrofuran; acetone; acetonitrile; 1.1: Esterification / 2.1: Reduction / 3.1: Substitution / 4.1: Benzylation / 5.1: Metallation / 5.2: Glycosylation;
DOI:10.1021/jm990320x

Reference yield:

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

: 286949-67-5
2-benzylthio-1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5,6-dichloroindole

Guidance literature:: Multi-step reaction with 4 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

With tetraphosphorus decasulfide; hydrogen; sodium hydride; potassium carbonate; acetic acid; platinum(IV) oxide; In tetrahydrofuran; acetone; acetonitrile; 1.1: Reduction / 2.1: Substitution / 3.1: Benzylation / 4.1: Metallation / 4.2: Glycosylation;
DOI:10.1021/jm990320x