2,9-Decadienoic acid, 5-[(4-methoxyphenyl)methoxy]-4,6-dimethyl-7-[(triethylsilyl)oxy]-, ethyl ester, (2E,4S,5R,6R,7R)-

Base Information

• Chemical Name: 2,9-Decadienoic acid, 5-[(4-methoxyphenyl)methoxy]-4,6-dimethyl-7-[(triethylsilyl)oxy]-, ethyl ester, (2E,4S,5R,6R,7R)-
• CAS No.: 201854-74-2
• Molecular Formula: C28H46O5Si
• Molecular Weight: 490.756
• Mol file: 201854-74-2.mol

Synonyms:

Chemical Property of 2,9-Decadienoic acid, 5-[(4-methoxyphenyl)methoxy]-4,6-dimethyl-7-[(triethylsilyl)oxy]-, ethyl ester, (2E,4S,5R,6R,7R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,9-Decadienoic acid, 5-[(4-methoxyphenyl)methoxy]-4,6-dimethyl-7-[(triethylsilyl)oxy]-, ethyl ester, (2E,4S,5R,6R,7R)-

There total 9 articles about 2,9-Decadienoic acid, 5-[(4-methoxyphenyl)methoxy]-4,6-dimethyl-7-[(triethylsilyl)oxy]-, ethyl ester, (2E,4S,5R,6R,7R)- 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:

(3S,4S,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene (106357-24-8) → (E)-(4S,5R,6R,7R)-5-(4-Methoxy-benzyloxy)-4,6-dimethyl-7-triethylsilanyloxy-deca-2,9-dienoic acid ethyl ester (201854-74-2)

Guidance literature:

Multi-step reaction with 10 steps

1: TfOH / diethyl ether

2: TBAF / tetrahydrofuran

3: DMAP, pyridine

4: OsO₄, NMO

5: NaIO₄ / tetrahydrofuran; H₂O

6: BF₃*Et₂O / -78 °C

7: 2,6-lutidine

8: DIBAL / hexane

9: Swern oxidation

10: NaHMDS

With pyridine; 2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; water;

DOI:10.1016/S0040-4039(97)10475-0

Reference yield:

3-((4-methoxybenzyl)oxy)-2,4-dimethylhex-5-enal (657389-50-9) → (E)-(4S,5R,6R,7R)-5-(4-Methoxy-benzyloxy)-4,6-dimethyl-7-triethylsilanyloxy-deca-2,9-dienoic acid ethyl ester (201854-74-2)

Guidance literature:

Multi-step reaction with 8 steps

1: DMAP, pyridine

2: OsO₄, NMO

3: NaIO₄ / tetrahydrofuran; H₂O

4: BF₃*Et₂O / -78 °C

5: 2,6-lutidine

6: DIBAL / hexane

7: Swern oxidation

8: NaHMDS

With pyridine; 2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; hexane; water;

DOI:10.1016/S0040-4039(97)10475-0

Reference yield:

Benzoic acid (2S,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-enyl ester (201854-70-8) → (E)-(4S,5R,6R,7R)-5-(4-Methoxy-benzyloxy)-4,6-dimethyl-7-triethylsilanyloxy-deca-2,9-dienoic acid ethyl ester (201854-74-2)

Guidance literature:

Multi-step reaction with 7 steps

1: OsO₄, NMO

2: NaIO₄ / tetrahydrofuran; H₂O

3: BF₃*Et₂O / -78 °C

4: 2,6-lutidine

5: DIBAL / hexane

6: Swern oxidation

7: NaHMDS

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; hexane; water;

DOI:10.1016/S0040-4039(97)10475-0

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

(3S,4S,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene

3-((4-methoxybenzyl)oxy)-2,4-dimethylhex-5-enal

Benzoic acid (2S,3S,4S)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-hex-5-enyl ester

Downstream raw materials:

1-[6-allyl-4-(4-methoxy-benzyloxy)-3,5-dimethyl-tetrahydropyran-2-yl]-ethane-1,2-diol

(E)-(4S,5R,6R,7R)-5-(4-Methoxy-benzyloxy)-4,6-dimethyl-7-triethylsilanyloxy-deca-2,9-dien-1-ol