3-benzyloxy-11-[1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-2-hydroxy-ethyl]-12-(tert-butyl-dimethyl-silanyloxymethyl)-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: 3-benzyloxy-11-[1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-2-hydroxy-ethyl]-12-(tert-butyl-dimethyl-silanyloxymethyl)-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.: 442663-55-0
• Molecular Formula: C₄₇H₅₅Cl₃N₂O₁₀Si
• Molecular Weight: 942.406
• Mol file: 442663-55-0.mol

Synonyms:3-benzyloxy-11-[1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-2-hydroxy-ethyl]-12-(tert-butyl-dimethyl-silanyloxymethyl)-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 3-benzyloxy-11-[1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-2-hydroxy-ethyl]-12-(tert-butyl-dimethyl-silanyloxymethyl)-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:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-benzyloxy-11-[1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-2-hydroxy-ethyl]-12-(tert-butyl-dimethyl-silanyloxymethyl)-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 43 articles about 3-benzyloxy-11-[1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-2-hydroxy-ethyl]-12-(tert-butyl-dimethyl-silanyloxymethyl)-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: 91.0%

benzyl bromide (100-39-0) + 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[7.3.1.02,7]trideca-2,4,6-triene-13-carboxylic acid 2,2,2-trichloro-ethyl ester (442663-54-9) → 3-benzyloxy-11-[1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-2-hydroxy-ethyl]-12-(tert-butyl-dimethyl-silanyloxymethyl)-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 (442663-55-0)

Guidance literature:

With potassium carbonate; In acetonitrile; for 1h; Heating;

DOI:10.1021/ja026216d

Reference yield:

alcohol (442663-47-0) → 3-benzyloxy-11-[1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-2-hydroxy-ethyl]-12-(tert-butyl-dimethyl-silanyloxymethyl)-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 (442663-55-0)

Guidance literature:

Multi-step reaction with 18 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

With pyridine; 1H-imidazole; quinoline; dmap; sodium hydroxide; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; guanidinium nitrate; TEA; sulfuric acid; camphor-10-sulfonic acid; sodium methylate; 3,3-dimethyldioxirane; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; methoxybenzene; 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) → 3-benzyloxy-11-[1-(6-benzyloxy-7-methyl-benzo[1,3]dioxol-4-yl)-2-hydroxy-ethyl]-12-(tert-butyl-dimethyl-silanyloxymethyl)-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 (442663-55-0)

Guidance literature:

Multi-step reaction with 29 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

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; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; sodium methylate; sodium acetate; 3,3-dimethyldioxirane; sodium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; methoxybenzene; 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:

benzyl bromide

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

Sesamol

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

(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

alcohol compound