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

Base Information

• Chemical Name: [(Z)-(3S,4S,5S)-2-Hydroxy-4-(4-methoxy-benzyloxy)-3,5-dimethyl-nona-6,8-dienyl]-phosphonic acid dimethyl ester
• CAS No.: 860477-26-5
• Molecular Formula: C₂₁H₃₃O₆P
• Molecular Weight: 412.463
• Mol file: 860477-26-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about [(Z)-(3S,4S,5S)-2-Hydroxy-4-(4-methoxy-benzyloxy)-3,5-dimethyl-nona-6,8-dienyl]-phosphonic acid dimethyl 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: 98.0%

(+)-(Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dienal (184291-97-2) + dimethyl methane phosphonate (756-79-6) → [(Z)-(3S,4S,5S)-2-Hydroxy-4-(4-methoxy-benzyloxy)-3,5-dimethyl-nona-6,8-dienyl]-phosphonic acid dimethyl ester (860477-26-5)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃;

(+)-(Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dienal; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

DOI:10.1016/j.tet.2010.01.083

Reference yield:

(2S,3S)-3-(Diisopropyl-prop-1-ynyl-silanyloxy)-2-methyl-pent-4-en-1-ol (887602-35-9) → [(Z)-(3S,4S,5S)-2-Hydroxy-4-(4-methoxy-benzyloxy)-3,5-dimethyl-nona-6,8-dienyl]-phosphonic acid dimethyl ester (860477-26-5)

Guidance literature:

Multi-step reaction with 11 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

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; triisopropoxytitanium(IV) chloride; dmap; 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

Reference yield:

(5S,6S)-6-[(S)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-5-methyl-5,6-dihydro-2H-pyran-2-ol → [(Z)-(3S,4S,5S)-2-Hydroxy-4-(4-methoxy-benzyloxy)-3,5-dimethyl-nona-6,8-dienyl]-phosphonic acid dimethyl ester (860477-26-5)

Guidance literature:

Multi-step reaction with 5 steps

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

1.2: 0.098 g / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

2.1: 78 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / 0 °C

3.1: DIBAL-H / CH₂Cl₂ / 3 h / 0 °C

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

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

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

With n-butyllithium; 4 A molecular sieve; diisobutylaluminium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexane; dichloromethane; 1.2: Wittig olefination;

DOI:10.1021/ja0609708

upstream raw materials:

(+)-(Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dienal

dimethyl methane phosphonate

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

(E)-(2S,3S,4S)-1-(4-Methoxy-benzyloxy)-2,4-dimethyl-hept-5-en-3-ol

Downstream raw materials:

(3Z,9E)-(5S,6S,7R,11R,13S,14R,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6,16-bis-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-1,3,9-trien-8-one

(3Z,16Z,22E)-(5S,6S,7R,11S,13S,14R,15S,18S,20S,21R)-14,18,20,24-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,16,22-tetraen-8-one

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

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