5-Nonenoic acid, 9-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-7-[(4-methoxyphenyl)methoxy]-4, 8-dimethyl-3-(phenylmethoxy)-, (3R,4S,5Z,7S,8R)-

Base Information

• Chemical Name: 5-Nonenoic acid, 9-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-7-[(4-methoxyphenyl)methoxy]-4, 8-dimethyl-3-(phenylmethoxy)-, (3R,4S,5Z,7S,8R)-
• CAS No.: 668421-79-2
• Molecular Formula: C42H52O6Si
• Molecular Weight: 680.957
• Mol file: 668421-79-2.mol

Synonyms:

Chemical Property of 5-Nonenoic acid, 9-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-7-[(4-methoxyphenyl)methoxy]-4, 8-dimethyl-3-(phenylmethoxy)-, (3R,4S,5Z,7S,8R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Nonenoic acid, 9-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-7-[(4-methoxyphenyl)methoxy]-4, 8-dimethyl-3-(phenylmethoxy)-, (3R,4S,5Z,7S,8R)-

There total 31 articles about 5-Nonenoic acid, 9-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-7-[(4-methoxyphenyl)methoxy]-4, 8-dimethyl-3-(phenylmethoxy)-, (3R,4S,5Z,7S,8R)- 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:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (3R,4S,7S,8R)-3-benzyloxy-9-(t-butyldiphenylsiloxy)-7-(p-methoxybenzyloxy)-4,8-dimethyl-cis-5-nonenoic acid (668421-79-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: CSA / CH₂Cl₂ / 2 h / 20 °C

2.1: TBAF / tetrahydrofuran / 1 h / 0 °C

3.1: NCS; K₂CO₃; N-t-butylbenzenesulfenamide / 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

4.1: NaHMDS / toluene / 0.08 h / 20 °C

4.2: toluene / 1 h / 20 °C

5.1: DIBAL / CH₂Cl₂ / 1.5 h / -10 °C

6.1: Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

7.1: aq. HCl / tetrahydrofuran / 48 h / 20 °C

8.1: DMP / CH₂Cl₂ / 0.5 h / 20 °C

9.1: TEMPO; NaClO₂; NaClO / aq. phosphate buffer; acetonitrile / 2.33 h / 35 °C / pH 7

With hydrogenchloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; N-chloro-succinimide; phthalic acid dimethyl ester; N-(phenylthio)-N-(tert-butyl)amine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; triethylamine; 4 A molecular sieve; In tetrahydrofuran; phosphate buffer; dichloromethane; toluene; acetonitrile;

DOI:10.1002/chem.200500417

Reference yield:

methyl 3-hydroxy-4-(triisopropylsiloxy)-2-methylbutanoate → (3R,4S,7S,8R)-3-benzyloxy-9-(t-butyldiphenylsiloxy)-7-(p-methoxybenzyloxy)-4,8-dimethyl-cis-5-nonenoic acid (668421-79-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 15 percent / DIBAL / CH₂Cl₂ / 1 h / 0 °C

2.1: 47 percent / DIBAL / CH₂Cl₂ / 1.5 h / 0 °C

3.1: CSA / CH₂Cl₂ / 2 h / 20 °C

4.1: TBAF / tetrahydrofuran / 1 h / 0 °C

5.1: NCS; K₂CO₃; N-t-butylbenzenesulfenamide / 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

6.1: NaHMDS / toluene / 0.08 h / 20 °C

6.2: toluene / 1 h / 20 °C

7.1: DIBAL / CH₂Cl₂ / 1.5 h / -10 °C

8.1: Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

9.1: aq. HCl / tetrahydrofuran / 48 h / 20 °C

10.1: DMP / CH₂Cl₂ / 0.5 h / 20 °C

11.1: TEMPO; NaClO₂; NaClO / aq. phosphate buffer; acetonitrile / 2.33 h / 35 °C / pH 7

With hydrogenchloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; N-chloro-succinimide; phthalic acid dimethyl ester; N-(phenylthio)-N-(tert-butyl)amine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; triethylamine; 4 A molecular sieve; In tetrahydrofuran; phosphate buffer; dichloromethane; toluene; acetonitrile;

DOI:10.1002/chem.200500417

Reference yield:

methyl (2R,3S)-3-hydroxy-4-(triisopropylsiloxy)-2-methyl-2-methylselenobutanoate → (3R,4S,7S,8R)-3-benzyloxy-9-(t-butyldiphenylsiloxy)-7-(p-methoxybenzyloxy)-4,8-dimethyl-cis-5-nonenoic acid (668421-79-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: iPr₂NEt; dibutylboron trifluoromethanesulfonate / toluene; CH₂Cl₂ / 0 - 20 °C

1.2: 77 percent / nBuSn₃H; Et₃B / toluene; hexane / 14 h / -78 °C

2.1: 15 percent / DIBAL / CH₂Cl₂ / 1 h / 0 °C

3.1: 47 percent / DIBAL / CH₂Cl₂ / 1.5 h / 0 °C

4.1: CSA / CH₂Cl₂ / 2 h / 20 °C

5.1: TBAF / tetrahydrofuran / 1 h / 0 °C

6.1: NCS; K₂CO₃; N-t-butylbenzenesulfenamide / 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

7.1: NaHMDS / toluene / 0.08 h / 20 °C

7.2: toluene / 1 h / 20 °C

8.1: DIBAL / CH₂Cl₂ / 1.5 h / -10 °C

9.1: Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

10.1: aq. HCl / tetrahydrofuran / 48 h / 20 °C

11.1: DMP / CH₂Cl₂ / 0.5 h / 20 °C

12.1: TEMPO; NaClO₂; NaClO / aq. phosphate buffer; acetonitrile / 2.33 h / 35 °C / pH 7

With hydrogenchloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; N-chloro-succinimide; phthalic acid dimethyl ester; N-(phenylthio)-N-(tert-butyl)amine; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 4 A molecular sieve; In tetrahydrofuran; phosphate buffer; dichloromethane; toluene; acetonitrile;

DOI:10.1002/chem.200500417

upstream raw materials:

(2S,3R)-1,3-[(S)-benzylidenedioxy]-5-(t-butyldimethylsiloxy)-2-methylpentane

(2S,3R)-3-benzyloxy-5-(t-butyldimethylsiloxy)-2-methylpentanol

(2R,3R)-1-(triisopropylsiloxy)-2,4-[(R)-p-methoxybenzylidenedioxy]-3-methylbutane

(3R,4S,7S,8R)-3-benzyloxy-7,9-[(R)-p-methoxybenzylidenedioxy]-4,8-dimethyl-1-(triisopropylsiloxy)-cis-5-nonene

Downstream raw materials:

(3R,4S,7S,8R)-3-benzyloxy-9-oxo-4,8-dimethylnonan-7-olide

(3S,4S,7S,8R)-3-benzyloxy-9-hydroxy-4,8-dimethylnonan-7-olide

(3R,4S,7S,8R)-3-benzyloxy-9-(tert-butyldiphenylsiloxy)-4,8-dimethylnonan-7-olide

(3R,4S,7S,8R)-3-benzyloxy-9-(tert-butyldiphenylsiloxy)-4,8-dimethyl-7-hydroxynonanoic acid