(2E,4E)-5-[(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester

Base Information

Chemical Name:(2E,4E)-5-[(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester
CAS No.:339291-67-7
Molecular Formula:C₃₁H₄₈O₅Si
Molecular Weight:528.805
Hs Code.:

(2E,4E)-5-[(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester

Synonyms:(2E,4E)-5-[(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester

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Chemical Property of (2E,4E)-5-[(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester

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Technology Process of (2E,4E)-5-[(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester

There total 11 articles about (2E,4E)-5-[(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic 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: 70.0%

: 67629-62-3
methyl 4-(diethylphosphono)crotonate

: 339291-66-6
(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentanecarbaldehyde

: 339291-67-7
(2E,4E)-5-[(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester

Guidance literature:: With lithium hydroxide; 4 A molecular sieve; In tetrahydrofuran; for 11h; Heating;
DOI:10.1021/jo005683f

Reference yield:

: 2403-58-9
4-methoxybenzaldehyde diethylacetal

: 339291-67-7
(2E,4E)-5-[(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 26.5 g / dimethylformamide / 3 h / 50 °C / 10 - 15 Torr

2.1: 83 percent / DIBAL / CH₂Cl₂; cyclohexane / 5 h / -78 °C

3.1: DMSO; oxalyl chloride; Et₃N

4.1: 18-crown-6/acetonitrile complex; KHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 1.788 g / tetrahydrofuran / 1 h / -78 °C

5.1: 97 percent / DIBAL / hexane; CH₂Cl₂ / -78 - 20 °C

6.1: 73 percent / DMAP / dimethylformamide / 20 °C

7.1: 93 percent / Dess-Martin perioninane / CH₂Cl₂ / 4 h / 20 °C

8.1: 70 percent / LiOH*H₂O; molecular sieves 4 Angstroeme / tetrahydrofuran / 11 h / Heating

With dmap; lithium hydroxide; oxalyl dichloride; 18-crown-6 ether; 4 A molecular sieve; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; acetonitrile; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; 3.1: Swern oxidation;
DOI:10.1021/jo005683f

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 339291-67-7
(2E,4E)-5-[(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 73 percent / DMAP / dimethylformamide / 20 °C

2: 93 percent / Dess-Martin perioninane / CH₂Cl₂ / 4 h / 20 °C

3: 70 percent / LiOH*H₂O; molecular sieves 4 Angstroeme / tetrahydrofuran / 11 h / Heating

With dmap; lithium hydroxide; 4 A molecular sieve; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo005683f