(1R,9S,10R,12R)-11-[(R)-2-Acetoxy-1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-10-cyano-12-formyl-4-methoxy-5-methyl-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,10R,12R)-11-[(R)-2-Acetoxy-1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-10-cyano-12-formyl-4-methoxy-5-methyl-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.: 442663-36-7
• Molecular Formula: C₄₄H₄₂Cl₃N₃O₁₀
• Molecular Weight: 879.191

Synonyms:(1R,9S,10R,12R)-11-[(R)-2-Acetoxy-1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-10-cyano-12-formyl-4-methoxy-5-methyl-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,10R,12R)-11-[(R)-2-Acetoxy-1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-10-cyano-12-formyl-4-methoxy-5-methyl-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:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,9S,10R,12R)-11-[(R)-2-Acetoxy-1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-10-cyano-12-formyl-4-methoxy-5-methyl-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 49 articles about (1R,9S,10R,12R)-11-[(R)-2-Acetoxy-1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-10-cyano-12-formyl-4-methoxy-5-methyl-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: 92.0%

alcohol compound (442663-58-3) → (1R,9S,10R,12R)-11-[(R)-2-Acetoxy-1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-10-cyano-12-formyl-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester (442663-36-7)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.666667h;

DOI:10.1021/ja026216d

Reference yield:

alcohol (442663-47-0) → (1R,9S,10R,12R)-11-[(R)-2-Acetoxy-1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-10-cyano-12-formyl-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester (442663-36-7)

Guidance literature:

Multi-step reaction with 23 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

16: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C

17: 85 percent / guanidinium nitrate; NaOMe / methanol; CH₂Cl₂ / 2.5 h / 40 °C

18: 91 percent / K₂CO₃ / acetonitrile / 1 h / Heating

19: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C

20: 73 percent / BF₃*OEt₂ / CH₂Cl₂ / 0 °C

21: 92 percent / pyridine; DMAP / 20 °C

22: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C

23: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 20 °C

With pyridine; 1H-imidazole; quinoline; dmap; sodium hydroxide; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; guanidinium nitrate; TEA; sulfuric acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen fluoride; sodium methylate; 3,3-dimethyldioxirane; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; methoxybenzene; sodium bis(2-methoxyethoxy)aluminium dihydride; tris-(o-tolyl)phosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 8: Heck reaction;

DOI:10.1021/ja026216d

Reference yield:

Sesamol (533-31-3) → (1R,9S,10R,12R)-11-[(R)-2-Acetoxy-1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-ethyl]-3-benzyloxy-10-cyano-12-formyl-4-methoxy-5-methyl-11,13-diaza-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester (442663-36-7)

Guidance literature:

Multi-step reaction with 34 steps

1.1: NaH / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 20 °C

1.2: 97 percent / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0 - 20 °C

2.2: 92 percent / aq. H₂O₂; trimethylboronate; AcOH / tetrahydrofuran; hexane / 4.5 h / 20 °C

3.1: 89 percent / TFA / CH₂Cl₂ / 2.17 h / -10 °C

4.1: 90 percent / pyridine / CH₂Cl₂ / 0.08 h / 0 °C

5.1: 85 percent / NaBH₄ / methanol / 0.5 h / 0 °C

6.1: 91 percent / imidazole / dimethylformamide / 20 °C

7.1: 97 percent / PdCl₂(dppf) / tetrahydrofuran / 4.5 h / Heating

8.1: Pb(OAc)4 / acetonitrile / 0 °C

9.1: 436 mg / NH₂OH*HCl; NaOAc / ethanol / 1.5 h / 20 °C

10.1: 90 percent / methanol / 1 h / Heating

11.1: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

12.1: 93 percent / pyridine; DMAP / 30 h / 50 °C

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

14.1: 19.7 g / ethyl acetate / 1 h / Heating

15.1: 91 percent / TEA / CH₂Cl₂ / 1 h / 0 °C

16.1: 97 percent / DMAP / acetonitrile / 6.5 h / 20 °C

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

18.1: 3.54 g / CSA; quinoline / toluene / 3 h / Heating

19.1: 83 percent / tris(dibenzylideneacetone)dipalladium⁽⁰⁾; tris(o-tolyl)phosphine; TEA / acetonitrile / 2 h / Heating

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

21.1: 106 mg / pyridine; DMAP / CH₂Cl₂ / 20 °C

22.1: TFA / CH₂Cl₂ / 4 h / 20 °C

23.1: 2.08 g / NaHCO₃ / CH₂Cl₂; H₂O / 0.17 h / 0 °C

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

25.1: 652 mg / CSA / acetone / 0 - 20 °C

26.1: 94 percent / sodium cyanoborohydride; TFA / tetrahydrofuran / 0.5 h / 0 °C

27.1: 92 percent / imidazole / dimethylformamide / 2 h / 20 °C

28.1: 85 percent / guanidinium nitrate; NaOMe / methanol; CH₂Cl₂ / 2.5 h / 40 °C

29.1: 91 percent / K₂CO₃ / acetonitrile / 1 h / Heating

30.1: 82 percent / Red-Al / tetrahydrofuran; toluene / 0 °C

31.1: 73 percent / BF₃*OEt₂ / CH₂Cl₂ / 0 °C

32.1: 92 percent / pyridine; DMAP / 20 °C

33.1: 100 percent / aq. HF / acetonitrile / 3 h / 20 °C

34.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 20 °C

With pyridine; 1H-imidazole; quinoline; lead(IV) acetate; dmap; sodium hydroxide; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; guanidinium nitrate; TEA; sulfuric acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen fluoride; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; sodium methylate; sodium acetate; 3,3-dimethyldioxirane; sodium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; methoxybenzene; sodium bis(2-methoxyethoxy)aluminium dihydride; tris-(o-tolyl)phosphine; trifluoroacetic acid; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 3.1: Mannich reaction / 10.1: Ugi reaction / 19.1: Heck reaction;

DOI:10.1021/ja026216d

upstream raw materials:

alcohol compound

Sesamol

benzyl bromide

3,4-(methylenedioxy)phenyl methoxymethyl ether

Downstream raw materials:

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

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