2-[1-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-meth-(E)-ylidene]-malonic acid monomethyl ester

Base Information

• Chemical Name: 2-[1-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-meth-(E)-ylidene]-malonic acid monomethyl ester
• CAS No.: 203922-28-5
• Molecular Formula: C₂₄H₄₀O₇Si₂
• Molecular Weight: 496.748
• Mol file: 203922-28-5.mol

Synonyms:2-[1-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-meth-(E)-ylidene]-malonic acid monomethyl ester

Chemical Property of 2-[1-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-meth-(E)-ylidene]-malonic acid monomethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[1-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-meth-(E)-ylidene]-malonic acid monomethyl ester

There total 1 articles about 2-[1-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-meth-(E)-ylidene]-malonic acid monomethyl 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:

Malonic acid monomethyl ester (16695-14-0) + 3,5-di-tert-butyldimethylsilyloxy-4-methoxybenzaldehyde (103929-82-4) → 2-[1-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-meth-(E)-ylidene]-malonic acid monomethyl ester (203922-28-5)

Guidance literature:

With piperidine; acetic acid; In benzene; at 23 ℃; for 18h;

DOI:10.1021/ja962480t

Reference yield:

2-[1-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-meth-(E)-ylidene]-malonic acid monomethyl ester (203922-28-5) → ecteinascidin 743 (114899-77-3)

Guidance literature:

Multi-step reaction with 25 steps

1: (PhO)2P(O)N₃, Et₃N, 4 Angstroem molecular sieves / toluene / 2 h / 70 °C

2: 1 h / 23 °C

3: H₂, Rh<(COD)-(R,R)-DIPAMP>(+)*BF₄(-) / 16 h / 23 °C / 2280 Torr

4: 90 percent / diisobutylaluminum hydride / CH₂Cl₂ / 1 h / -78 °C

5: 61 percent / HOAc / 18 h / 23 °C

6: 87 percent / Cs₂CO₃ / dimethylformamide / 1 h / 23 °C

7: diisobutylaluminum hydride / toluene / 5 h / -78 °C

8: KF*2H₂O / methanol / 0.33 h / 23 °C

9: CH₃SO₃H, 3 Angstroem molecular sieves / CH₂Cl₂ / 5 h / 23 °C

10: 72 percent / Et₃N, DMAP / CH₂Cl₂ / 6 h / 23 °C

11: 89 percent / DMAP / CH₂Cl₂ / 13 h / 23 °C

12: 92 percent / i-Pr₂NEt / CH₂Cl₂ / 0.33 h / 23 °C

13: 1.) Bu₃SnH, PdCl₂(PPh₃)2, HOAc, 2.) NaBH₃CN, HOAc / 1.) CH₂Cl₂, 23 deg C, 15 min, 2.) CH₃CN, 23 deg C, 30 min

14: 83 percent / PdCl₂(PPh₃)2, LiCl / dimethylformamide / 2 h / 80 °C

15: (PhSeO)2O / CH₂Cl₂ / 0.25 h / 23 °C

16: Bu₄NF / tetrahydrofuran / 0.17 h / 23 °C

17: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP / CH₂Cl₂ / 0.5 h / 23 °C

18: 0.5 h / -40 °C

19: 1.) i-Pr₂NEt, 2.) tert-butyl alcohol, N-tert-butyl-N',N',N'',N''-tetramethylguanidine / 1.) 0 deg C, 30 min, 2.) 23 deg C

20: 23 °C

21: 84 percent / PdCl₂(PPh₃)2, Bu₃SnH, HOAc / CH₂Cl₂ / 0.08 h / 23 °C

22: 70 percent / iodide, 1,8-diazabicyclo<6.4.0>undec-7-ene, DMF / CH₂Cl₂ / 0.67 h / 23 °C

23: 82 percent / silica gel / ethanol / 23 °C

24: aq. CF₃COOH / tetrahydrofuran / 9 h / 23 °C

25: aq. AgNO₃ / acetonitrile / 11 h / 23 °C

With dmap; bis-triphenylphosphine-palladium(II) chloride; potassium fluoride; methanesulfonic acid; Rh<(COD)-(R,R)-DIPAMP>(+)*BF4(-); (PhSeO)2O; 3 A molecular sieve; 4 A molecular sieve; diphenyl phosphoryl azide; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; N-methylpyridine-4-carboxaldehyde iodide; silica gel; diisobutylaluminium hydride; sodium cyanoborohydride; caesium carbonate; silver nitrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trifluoroacetic acid; lithium chloride; tert-butyl alcohol; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja962480t

Reference yield:

2-[1-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-meth-(E)-ylidene]-malonic acid monomethyl ester (203922-28-5) → (Z)-3-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-2-isocyanato-acrylic acid methyl ester

Guidance literature:

With 4 A molecular sieve; diphenyl phosphoryl azide; triethylamine; In toluene; at 70 ℃; for 2h;

DOI:10.1021/ja962480t

upstream raw materials:

Malonic acid monomethyl ester

3,5-di-tert-butyldimethylsilyloxy-4-methoxybenzaldehyde

Downstream raw materials:

{(S)-2-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-1-formyl-ethyl}-carbamic acid allyl ester

(S)-2-Allyloxycarbonylamino-3-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-propionic acid methyl ester

C₃₁H₃₅N₃O₁₀

C₄₀H₅₇N₃O₁₀Si₂