(7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undecanoate

Base Information

Chemical Name:(7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undecanoate
CAS No.:276880-19-4
Molecular Formula:C₂₃H₃₉O₈P
Molecular Weight:474.532
Hs Code.:

Synonyms:(7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undecanoate

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

Chemical Property:

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

There total 15 articles about (7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undecanoate 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: 99.0%

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

: 276880-19-4
(7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undecanoate

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate;
DOI:10.1021/ja000429q

Reference yield:

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

: 276880-19-4
(7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undecanoate

Guidance literature:: Multi-step reaction with 15 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

15.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 5 h

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; ethyl acetate; 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 / 15.1: Catalytic hydrogenation;
DOI:10.1021/ja000429q

Reference yield:

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

: 276880-19-4
(7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undecanoate

Guidance literature:: Multi-step reaction with 13 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

13.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 5 h

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; ethyl acetate; 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 / 13.1: Catalytic hydrogenation;
DOI:10.1021/ja000429q