[1(3Z,5R,6S,7S,9E),3R,4E]-3-methoxy-hepta-4,6-dienoic acid {3-[7-(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-dodeca-3,9,11-trienyl]-2,5-dimethoxy-phenyl}-amide

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Chemical Name:[1(3Z,5R,6S,7S,9E),3R,4E]-3-methoxy-hepta-4,6-dienoic acid {3-[7-(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-dodeca-3,9,11-trienyl]-2,5-dimethoxy-phenyl}-amide
CAS No.:669065-35-4
Molecular Formula:C₄₅H₇₇NO₆Si₂
Molecular Weight:784.28
Hs Code.:

[1(3Z,5R,6S,7S,9E),3R,4E]-3-methoxy-hepta-4,6-dienoic acid {3-[7-(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-dodeca-3,9,11-trienyl]-2,5-dimethoxy-phenyl}-amide

Synonyms:[1(3Z,5R,6S,7S,9E),3R,4E]-3-methoxy-hepta-4,6-dienoic acid {3-[7-(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-dodeca-3,9,11-trienyl]-2,5-dimethoxy-phenyl}-amide

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Chemical Property of [1(3Z,5R,6S,7S,9E),3R,4E]-3-methoxy-hepta-4,6-dienoic acid {3-[7-(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-dodeca-3,9,11-trienyl]-2,5-dimethoxy-phenyl}-amide

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Technology Process of [1(3Z,5R,6S,7S,9E),3R,4E]-3-methoxy-hepta-4,6-dienoic acid {3-[7-(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-dodeca-3,9,11-trienyl]-2,5-dimethoxy-phenyl}-amide

There total 27 articles about [1(3Z,5R,6S,7S,9E),3R,4E]-3-methoxy-hepta-4,6-dienoic acid {3-[7-(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-dodeca-3,9,11-trienyl]-2,5-dimethoxy-phenyl}-amide 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: 75.0%

: (E)-(R)-3-Methoxy-6-oxo-hex-4-enoic acid {3-[(3Z,9E)-(5R,6S,7S)-7-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-11-oxo-5-triisopropylsilanyloxy-undeca-3,9-dienyl]-2,5-dimethoxy-phenyl}-(2,2,2-trichloro-ethoxymethyl)-amide

: 669065-35-4
[1(3Z,5R,6S,7S,9E),3R,4E]-3-methoxy-hepta-4,6-dienoic acid {3-[7-(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-dodeca-3,9,11-trienyl]-2,5-dimethoxy-phenyl}-amide

Guidance literature:: With disodium hydrogenphosphate; sodium amalgam; In methanol; at -30 - -20 ℃; for 1.33333h;
DOI:10.1021/ol036284k

Reference yield:

: 669065-40-1
(R)-4-(tert-butyldimethylsilyloxy)-3-methoxy-butyric acid benzyl ester

: 669065-35-4
[1(3Z,5R,6S,7S,9E),3R,4E]-3-methoxy-hepta-4,6-dienoic acid {3-[7-(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-dodeca-3,9,11-trienyl]-2,5-dimethoxy-phenyl}-amide

Guidance literature:: Multi-step reaction with 12 steps

1.1: 100 percent / H₂ / Pd/C / methanol / 1.5 h

2.1: Et₃N; ClCO₂Et / CH₂Cl₂ / 0.67 h / -20 °C

2.2: 91 percent / NH₃ gas / CH₂Cl₂ / -10 °C

3.1: 82 percent / K₂CO₃; CuI; N,N'-dimethylethylenediamine / toluene / 36 h / 110 °C

4.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 73 percent / tetrahydrofuran / 8 h / -78 - -30 °C

5.1: 96 percent / Na₂HPO₄; Na/Hg / methanol / 1.5 h / -20 °C

6.1: KH / tetrahydrofuran / 0.15 h / 0 °C

6.2: 95 percent / tetrahydrofuran / 0.33 h / 20 °C

7.1: 91 percent / HF*pyr / pyridine; tetrahydrofuran / 2 h / 0 - 20 °C

8.1: 91 percent / Et₃N; SO₃*pyr / dimethylsulfoxide / 1.33 h / 20 °C

9.1: CH₂Cl₂ / 20 h / 20 °C

10.1: DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

11.1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

12.1: 75 percent / Na₂HPO₄; Na/Hg / methanol / 1.33 h / -30 - -20 °C

With disodium hydrogenphosphate; sodium amalgam; copper(l) iodide; oxalyl dichloride; pyridine-SO₃ complex; hydrogen; chloroformic acid ethyl ester; potassium hydride; diisobutylaluminium hydride; potassium carbonate; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; N,N`-dimethylethylenediamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; dimethyl sulfoxide; toluene; 8.1: Parikh-Doering oxidation / 9.1: Wittig reaction / 11.1: Swern oxidation;
DOI:10.1021/ol036284k

Reference yield:

: 672-13-9
2-hydroxy-5-methoxybenzaldehyde

: 669065-35-4
[1(3Z,5R,6S,7S,9E),3R,4E]-3-methoxy-hepta-4,6-dienoic acid {3-[7-(tert-butyl-dimethylsilyloxy)-4,6-dimethyl-5-triisopropylsilyloxy-dodeca-3,9,11-trienyl]-2,5-dimethoxy-phenyl}-amide

Guidance literature:: Multi-step reaction with 15 steps

1.1: 89 percent / AcONa; Br₂ / acetic acid / 1 h / 20 °C

2.1: 99 percent / K₂CO₃ / dimethylformamide / 24 h / 20 °C

3.1: 100 percent / BH₃*THF / tetrahydrofuran / 1 h / 0 °C

4.1: 96 percent / PPh₄; CBr₄ / tetrahydrofuran / 1 h / 20 °C

5.1: 86 percent / dimethylformamide / 24 h / 20 °C

6.1: 82 percent / K₂CO₃; CuI; N,N'-dimethylethylenediamine / toluene / 36 h / 110 °C

7.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

7.2: 73 percent / tetrahydrofuran / 8 h / -78 - -30 °C

8.1: 96 percent / Na₂HPO₄; Na/Hg / methanol / 1.5 h / -20 °C

9.1: KH / tetrahydrofuran / 0.15 h / 0 °C

9.2: 95 percent / tetrahydrofuran / 0.33 h / 20 °C

10.1: 91 percent / HF*pyr / pyridine; tetrahydrofuran / 2 h / 0 - 20 °C

11.1: 91 percent / Et₃N; SO₃*pyr / dimethylsulfoxide / 1.33 h / 20 °C

12.1: CH₂Cl₂ / 20 h / 20 °C

13.1: DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

14.1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

15.1: 75 percent / Na₂HPO₄; Na/Hg / methanol / 1.33 h / -30 - -20 °C

With disodium hydrogenphosphate; sodium amalgam; copper(l) iodide; borane-THF; oxalyl dichloride; pyridine-SO₃ complex; carbon tetrabromide; bromine; sodium acetate; tetraphenylphosphonium; potassium hydride; diisobutylaluminium hydride; potassium carbonate; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; N,N`-dimethylethylenediamine; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 11.1: Parikh-Doering oxidation / 12.1: Wittig reaction / 14.1: Swern oxidation;
DOI:10.1021/ol036284k