(4E,7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undec-4-enoate

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Chemical Name:(4E,7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undec-4-enoate
CAS No.:276880-18-3
Molecular Formula:C₂₃H₃₇O₈P
Molecular Weight:472.516
Hs Code.:

Synonyms:(4E,7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undec-4-enoate

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Chemical Property of (4E,7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undec-4-enoate

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Technology Process of (4E,7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undec-4-enoate

There total 14 articles about (4E,7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undec-4-enoate 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%

: 276880-17-2
(4E,7S)-methyl 7-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}-2-(dimethoxyphosphoryl)undec-4-enoate

: 276880-18-3
(4E,7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undec-4-enoate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;
DOI:10.1021/ja000429q

Reference yield:

: 61367-62-2
(4-bromo-3,5-dimethoxyphenyl)methanol

: 276880-18-3
(4E,7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undec-4-enoate

Guidance literature:: Multi-step reaction with 14 steps

1.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / -20 - 20 °C

2.1: t-BuLi / ethanol; pentane / 0.5 h / -78 °C

2.2: 92 percent / ethanol; pentane / -78 - 20 °C

3.1: 70 percent / DBU; lithium chloride / acetonitrile / 36 h

4.1: 97 percent / NaBH₄; CeCl₃*7H₂O / ethanol / 0 °C

5.1: Amano P-30 lipase; 4A molecular sieves / hexane / 12 h / 20 °C

6.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C

6.2: 80 percent / tetrahydrofuran / -78 - 20 °C

7.1: 95 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

8.1: 99 percent / hydrogen / Pd/C / ethanol

9.1: 90 percent / DMSO; oxaloyl chloride; Et₃N / CH₂Cl₂ / -60 - 20 °C

10.1: 80 percent / DBU; LiCl / acetonitrile / 0 - 20 °C

11.1: 95 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

12.1: 89 percent / N-chlorosuccinimide; dimethyl sulfide / CH₂Cl₂ / -30 - 0 °C

13.1: 80 percent / potassium tert-butoxide / dimethylsulfoxide / 14 h

14.1: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

With dmap; sodium tetrahydroborate; N-chloro-succinimide; cerium(III) chloride; oxalyl dichloride; dimethylsulfide; 4 A molecular sieve; Amano P-30 lipase; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; pentane; 1.1: sililation / 2.1: Metallation / 2.2: Formylation / 3.1: Masamune olefination / 4.1: Reduction / 5.1: enzymatic acetylation / 6.1: Metallation / 6.2: sigmatropic rearrangement / 7.1: Reduction / 8.1: Catalytic hydrogenation / 9.1: Oxidation / 10.1: Masamune olefination / 11.1: Reduction / 12.1: Chlorination / 13.1: Alkylation / 14.1: desilylation;
DOI:10.1021/ja000429q

Reference yield:

: 276880-05-8
2,6-dimethoxy-4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzaldehyde

: 276880-18-3
(4E,7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undec-4-enoate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 70 percent / DBU; lithium chloride / acetonitrile / 36 h

2.1: 97 percent / NaBH₄; CeCl₃*7H₂O / ethanol / 0 °C

3.1: Amano P-30 lipase; 4A molecular sieves / hexane / 12 h / 20 °C

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

4.2: 80 percent / tetrahydrofuran / -78 - 20 °C

5.1: 95 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

6.1: 99 percent / hydrogen / Pd/C / ethanol

7.1: 90 percent / DMSO; oxaloyl chloride; Et₃N / CH₂Cl₂ / -60 - 20 °C

8.1: 80 percent / DBU; LiCl / acetonitrile / 0 - 20 °C

9.1: 95 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

10.1: 89 percent / N-chlorosuccinimide; dimethyl sulfide / CH₂Cl₂ / -30 - 0 °C

11.1: 80 percent / potassium tert-butoxide / dimethylsulfoxide / 14 h

12.1: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 - 20 °C

With sodium tetrahydroborate; N-chloro-succinimide; cerium(III) chloride; oxalyl dichloride; dimethylsulfide; 4 A molecular sieve; Amano P-30 lipase; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; 1.1: Masamune olefination / 2.1: Reduction / 3.1: enzymatic acetylation / 4.1: Metallation / 4.2: sigmatropic rearrangement / 5.1: Reduction / 6.1: Catalytic hydrogenation / 7.1: Oxidation / 8.1: Masamune olefination / 9.1: Reduction / 10.1: Chlorination / 11.1: Alkylation / 12.1: desilylation;
DOI:10.1021/ja000429q