14,18,20,24-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,9,16,22-pentaen-8-one

Base Information

• Chemical Name: 14,18,20,24-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,9,16,22-pentaen-8-one
• CAS No.: 887602-31-5
• Molecular Formula: C₆₂H₁₁₄O₇Si₄
• Molecular Weight: 1083.92
• Mol file: 887602-31-5.mol

Synonyms:14,18,20,24-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,9,16,22-pentaen-8-one

Chemical Property of 14,18,20,24-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,9,16,22-pentaen-8-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 14,18,20,24-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,9,16,22-pentaen-8-one

There total 30 articles about 14,18,20,24-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,9,16,22-pentaen-8-one 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%

[4-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-nona-6,8-dienyl]-phosphonic-acid dimethyl ester (792911-20-7) + (7Z,13E)-(2R,4S,5R,6S,9S,11S,12R)-5,9,11,15-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-pentadeca-7,13-dienal (887602-30-4) → 14,18,20,24-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,9,16,22-pentaen-8-one (887602-31-5)

Guidance literature:

[4-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-nona-6,8-dienyl]-phosphonic-acid dimethyl ester; With barium dihydroxide; In tetrahydrofuran; at 20 - 120 ℃; for 2h;

(7Z,13E)-(2R,4S,5R,6S,9S,11S,12R)-5,9,11,15-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-pentadeca-7,13-dienal; In tetrahydrofuran; water; for 6h;

DOI:10.1021/ja0609708

Reference yield:

[(Z)-(3S,4S,5S)-2-Hydroxy-4-(4-methoxy-benzyloxy)-3,5-dimethyl-nona-6,8-dienyl]-phosphonic acid dimethyl ester (860477-26-5) → 14,18,20,24-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,9,16,22-pentaen-8-one (887602-31-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 62 mg / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

2.1: Ba(OH)2*8H₂O / tetrahydrofuran / 2 h / 20 - 120 °C

2.2: 80 percent / tetrahydrofuran; H₂O / 6 h

With barium dihydroxide; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0609708

Reference yield:

(2S,3S)-3-(Diisopropyl-prop-1-ynyl-silanyloxy)-2-methyl-pent-4-en-1-ol (887602-35-9) → 14,18,20,24-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,9,16,22-pentaen-8-one (887602-31-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 82 percent / CSA / CH₂Cl₂ / -10 - 20 °C

2.1: 65 percent / Ti(i-PrO)3Cl; i-PrMgCl / diethyl ether / 6 h

3.1: TBAF*H₂O / dimethylformamide / 6 h / 75 °C

4.1: 0.131 g / i-Pr₂NEt; DMAP / CH₂Cl₂ / 0 - 20 °C

5.1: Grubbs 2nd catalyst / toluene / 3 h / 60 °C

6.1: DIBAL-H / toluene / 0.25 h / -78 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 0 °C

7.2: 0.098 g / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

8.1: 78 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / 0 °C

9.1: DIBAL-H / CH₂Cl₂ / 3 h / 0 °C

10.1: Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 0 °C

11.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

11.2: tetrahydrofuran; hexane / 0.75 h / -78 - 0 °C

12.1: 62 mg / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

13.1: Ba(OH)2*8H₂O / tetrahydrofuran / 2 h / 20 - 120 °C

13.2: 80 percent / tetrahydrofuran; H₂O / 6 h

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triisopropoxytitanium(IV) chloride; dmap; barium dihydroxide; n-butyllithium; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; isopropylmagnesium chloride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 7.2: Wittig olefination;

DOI:10.1021/ja0609708

upstream raw materials:

[4-(4-methoxy-benzyloxy)-3,5-dimethyl-2-oxo-nona-6,8-dienyl]-phosphonic-acid dimethyl ester

(7Z,13E)-(2R,4S,5R,6S,9S,11S,12R)-5,9,11,15-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-2,4,6,12-tetramethyl-pentadeca-7,13-dienal

[(Z)-(3S,4S,5S)-2-Hydroxy-4-(4-methoxy-benzyloxy)-3,5-dimethyl-nona-6,8-dienyl]-phosphonic acid dimethyl ester

(2S,3S)-3-(Diisopropyl-prop-1-ynyl-silanyloxy)-2-methyl-pent-4-en-1-ol