(1R,9S,12R)-11-[(R)-2-Acetoxy-1-(6-acetoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-12-hydroxymethyl-4-methoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester

Base Information

• Chemical Name: (1R,9S,12R)-11-[(R)-2-Acetoxy-1-(6-acetoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-12-hydroxymethyl-4-methoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester
• CAS No.: 442663-34-5
• Molecular Formula: C₃₈H₃₉Cl₃N₂O₁₂
• Molecular Weight: 822.093

Synonyms:(1R,9S,12R)-11-[(R)-2-Acetoxy-1-(6-acetoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-12-hydroxymethyl-4-methoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester

Chemical Property of (1R,9S,12R)-11-[(R)-2-Acetoxy-1-(6-acetoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-12-hydroxymethyl-4-methoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester

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Technology Process of (1R,9S,12R)-11-[(R)-2-Acetoxy-1-(6-acetoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-12-hydroxymethyl-4-methoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester

There total 42 articles about (1R,9S,12R)-11-[(R)-2-Acetoxy-1-(6-acetoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-12-hydroxymethyl-4-methoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester 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: 94.0%

(1R,9S,12S)-11-[(R)-2-Acetoxy-1-(6-acetoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-12-hydroxymethyl-4,12-dimethoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester → (1R,9S,12R)-11-[(R)-2-Acetoxy-1-(6-acetoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-12-hydroxymethyl-4-methoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester (442663-34-5)

Guidance literature:

With sodium cyanoborohydride; trifluoroacetic acid; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/ja026216d

Reference yield: 7.4%

methoxy compound → (1R,9S,12R)-11-[(R)-2-Acetoxy-1-(6-acetoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-12-hydroxymethyl-4-methoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester (442663-34-5)

Guidance literature:

With sodium cyanoborohydride; In tetrahydrofuran; trifluoroacetic acid; at 0 ℃; for 0.666667h;

Reference yield:

alcohol (442663-47-0) → (1R,9S,12R)-11-[(R)-2-Acetoxy-1-(6-acetoxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-12-hydroxymethyl-4-methoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester (442663-34-5)

Guidance literature:

Multi-step reaction with 15 steps

1: 93 percent / pyridine; DMAP / 30 h / 50 °C

2: TFA; anisole / CH₂Cl₂ / 9 h / 20 °C

3: 19.7 g / ethyl acetate / 1 h / Heating

4: 91 percent / TEA / CH₂Cl₂ / 1 h / 0 °C

5: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C

6: NaBH₄; H₂SO₄ / ethanol; CH₂Cl₂ / 0 °C

7: 3.54 g / CSA; quinoline / toluene / 3 h / Heating

8: 83 percent / tris(dibenzylideneacetone)dipalladium⁽⁰⁾; tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating

9: aq. NaOH / methanol / 2.5 h / Heating

10: 106 mg / pyridine; DMAP / CH₂Cl₂ / 20 °C

11: TFA / CH₂Cl₂ / 4 h / 20 °C

12: 2.08 g / NaHCO₃ / CH₂Cl₂; H₂O / 0.17 h / 0 °C

13: dimethyldioxirane / methanol; acetone / 2 h / 0 °C

14: 652 mg / CSA / acetone / 0 - 20 °C

15: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; quinoline; dmap; sodium hydroxide; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; TEA; sulfuric acid; camphor-10-sulfonic acid; 3,3-dimethyldioxirane; sodium cyanoborohydride; sodium hydrogencarbonate; methoxybenzene; tris-(o-tolyl)phosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile; 8: Heck reaction;

DOI:10.1021/ja026216d

upstream raw materials:

Sesamol

benzyl bromide

3,4-(methylenedioxy)phenyl methoxymethyl ether

3-methylbenzene-1,2-diol

Downstream raw materials:

silanylether

ecteinascidin 743

(1'R,6R,6aR,7R,13S,14R,16R)-5-(acetyloxy)-3',4',6,6a,7,13,14,16-octahydro-6',8-dihydroxy-7',9-dimethoxy-4,10,23-trimethyl-19-oxo-spiro[6,16-(epithiopropanoxymethano)-7,13-imino-12H-1,3-dioxolo[7,8]isoquino[3,2-b][3]benzazocine-20,1'(2'H)-isoquinoline]-14-carbonitrile

3-benzyloxy-12-(tert-butyl-dimethyl-silanyloxymethyl)-11-[2-hydroxy-1-(6-hydroxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-4-methoxy-5-methyl-10-oxo-11,13-diaza-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester

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