(2Z,4E,10E,12E)-(6R,7S,8S,14S,15R,16S,17S,18R,19R)-17-(tert-Butyl-dimethyl-silanyloxy)-19-(3,4-dimethoxy-benzyloxy)-7-hydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethyl-15-triethylsilanyloxy-icosa-2,4,10,12-tetraenoic acid methyl ester

Base Information

Chemical Name:(2Z,4E,10E,12E)-(6R,7S,8S,14S,15R,16S,17S,18R,19R)-17-(tert-Butyl-dimethyl-silanyloxy)-19-(3,4-dimethoxy-benzyloxy)-7-hydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethyl-15-triethylsilanyloxy-icosa-2,4,10,12-tetraenoic acid methyl ester
CAS No.:442899-68-5
Molecular Formula:C₅₀H₈₈O₁₀Si₂
Molecular Weight:905.414
Hs Code.:

(2Z,4E,10E,12E)-(6R,7S,8S,14S,15R,16S,17S,18R,19R)-17-(tert-Butyl-dimethyl-silanyloxy)-19-(3,4-dimethoxy-benzyloxy)-7-hydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethyl-15-triethylsilanyloxy-icosa-2,4,10,12-tetraenoic acid methyl ester

Synonyms:(2Z,4E,10E,12E)-(6R,7S,8S,14S,15R,16S,17S,18R,19R)-17-(tert-Butyl-dimethyl-silanyloxy)-19-(3,4-dimethoxy-benzyloxy)-7-hydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethyl-15-triethylsilanyloxy-icosa-2,4,10,12-tetraenoic acid methyl ester

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Chemical Property of (2Z,4E,10E,12E)-(6R,7S,8S,14S,15R,16S,17S,18R,19R)-17-(tert-Butyl-dimethyl-silanyloxy)-19-(3,4-dimethoxy-benzyloxy)-7-hydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethyl-15-triethylsilanyloxy-icosa-2,4,10,12-tetraenoic acid methyl ester

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Technology Process of (2Z,4E,10E,12E)-(6R,7S,8S,14S,15R,16S,17S,18R,19R)-17-(tert-Butyl-dimethyl-silanyloxy)-19-(3,4-dimethoxy-benzyloxy)-7-hydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethyl-15-triethylsilanyloxy-icosa-2,4,10,12-tetraenoic acid methyl ester

There total 17 articles about (2Z,4E,10E,12E)-(6R,7S,8S,14S,15R,16S,17S,18R,19R)-17-(tert-Butyl-dimethyl-silanyloxy)-19-(3,4-dimethoxy-benzyloxy)-7-hydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethyl-15-triethylsilanyloxy-icosa-2,4,10,12-tetraenoic acid methyl 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: 80.0%

: 243468-74-8
methyl (2Z,4E,10E,6R,7S,8S)-7-hydroxy-11-iodo-2-methoxy-4,6,8,10-tetramethyl-2,4,10-undecatrienoate

: 442899-64-1
C₃₃H₆₃BO₈Si₂

: 442899-68-5
(2Z,4E,10E,12E)-(6R,7S,8S,14S,15R,16S,17S,18R,19R)-17-(tert-Butyl-dimethyl-silanyloxy)-19-(3,4-dimethoxy-benzyloxy)-7-hydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethyl-15-triethylsilanyloxy-icosa-2,4,10,12-tetraenoic acid methyl ester

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; In tetrahydrofuran;
DOI:10.1021/ja017885e

Reference yield:

: 209251-62-7
(2R,3S,4S)-1-[(para-methoxybenxyl)oxy]-2,4-dimethyl-3-hexanol

: 442899-68-5
(2Z,4E,10E,12E)-(6R,7S,8S,14S,15R,16S,17S,18R,19R)-17-(tert-Butyl-dimethyl-silanyloxy)-19-(3,4-dimethoxy-benzyloxy)-7-hydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethyl-15-triethylsilanyloxy-icosa-2,4,10,12-tetraenoic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 2,6-lutidine

2.1: catecholborane; (Ph₃P)3RhCl

2.2: 86 percent / H₂O₂; NaOH

3.1: (COCl)2; DMSO; Et₃N / -78 °C

4.1: PPh₃

4.2: BuLi / tetrahydrofuran / -78 °C

5.1: 96 percent / DDQ / CH₂Cl₂ / pH 7

6.1: Cp₂ZrCl₂ / 1,2-dichloro-ethane / 60 °C

6.2: 65 percent / I₂ / tetrahydrofuran

7.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂

8.1: toluene / 60 °C

9.1: DIBAL / -78 °C

10.1: MnO₂ / CH₂Cl₂

11.1: 85 percent / KN(SiMe₃)2; 18-crown-6 / tetrahydrofuran

12.1: 82 percent / TBAF / tetrahydrofuran

13.1: 80 percent / TlOH; Pd(PPh₃)4 / tetrahydrofuran

With 2,6-dimethylpyridine; manganese(IV) oxide; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; zirconocene dichloride; TlOH; oxalyl dichloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene; 3.1: Moffatt-Swern oxidation / 6.1: Negishi reaction / 7.1: Moffatt-Swern oxidation / 8.1: Wittig olefination / 11.1: Horner-Wadsworth-Emmons reaction / 13.1: Suzuki coupling;
DOI:10.1021/ja017885e

Reference yield:

: 243468-90-8
(2R,3S,4S)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-6-heptyn-1-ol

: 442899-68-5
(2Z,4E,10E,12E)-(6R,7S,8S,14S,15R,16S,17S,18R,19R)-17-(tert-Butyl-dimethyl-silanyloxy)-19-(3,4-dimethoxy-benzyloxy)-7-hydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethyl-15-triethylsilanyloxy-icosa-2,4,10,12-tetraenoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: Cp₂ZrCl₂ / 1,2-dichloro-ethane / 60 °C

1.2: 65 percent / I₂ / tetrahydrofuran

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂

3.1: toluene / 60 °C

4.1: DIBAL / -78 °C

5.1: MnO₂ / CH₂Cl₂

6.1: 85 percent / KN(SiMe₃)2; 18-crown-6 / tetrahydrofuran

7.1: 82 percent / TBAF / tetrahydrofuran

8.1: 80 percent / TlOH; Pd(PPh₃)4 / tetrahydrofuran

With manganese(IV) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; zirconocene dichloride; TlOH; oxalyl dichloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene; 1.1: Negishi reaction / 2.1: Moffatt-Swern oxidation / 3.1: Wittig olefination / 6.1: Horner-Wadsworth-Emmons reaction / 8.1: Suzuki coupling;
DOI:10.1021/ja017885e