Nonanoic acid, 9-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-7-hydroxy-4,8-dimethyl-3-(phenyl methoxy)-, (3R,4S,7S,8R)-

Base Information

• Chemical Name: Nonanoic acid, 9-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-7-hydroxy-4,8-dimethyl-3-(phenyl methoxy)-, (3R,4S,7S,8R)-
• CAS No.: 668421-68-9
• Molecular Formula: C34H46O5Si
• Molecular Weight: 562.822
• Mol file: 668421-68-9.mol

Synonyms:

Chemical Property of Nonanoic acid, 9-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-7-hydroxy-4,8-dimethyl-3-(phenyl methoxy)-, (3R,4S,7S,8R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Nonanoic acid, 9-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-7-hydroxy-4,8-dimethyl-3-(phenyl methoxy)-, (3R,4S,7S,8R)-

There total 32 articles about Nonanoic acid, 9-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-7-hydroxy-4,8-dimethyl-3-(phenyl methoxy)-, (3R,4S,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: 83.0%

(3R,4S,7S,8R)-3-benzyloxy-9-(t-butyldiphenylsiloxy)-7-hydroxy-4,8-dimethyl-cis-5-nonenoic acid (861700-68-7) → (3R,4S,7S,8R)-3-benzyloxy-9-(tert-butyldiphenylsiloxy)-4,8-dimethyl-7-hydroxynonanoic acid (668421-68-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃;

DOI:10.1016/j.tetlet.2003.10.213

Reference yield:

methyl 3-hydroxy-4-(triisopropylsiloxy)-2-methylbutanoate → (3R,4S,7S,8R)-3-benzyloxy-9-(tert-butyldiphenylsiloxy)-4,8-dimethyl-7-hydroxynonanoic acid (668421-68-9)

Guidance literature:

Multi-step reaction with 13 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

12.1: aq. CAN / acetonitrile / 0.12 h / 0 °C

13.1: H₂; Et₃N / Pd/C / methanol / 20 h / 20 °C

With hydrogenchloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; N-chloro-succinimide; ammonium cerium(IV) nitrate; phthalic acid dimethyl ester; N-(phenylthio)-N-(tert-butyl)amine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; 4 A molecular sieve; In tetrahydrofuran; methanol; 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-(tert-butyldiphenylsiloxy)-4,8-dimethyl-7-hydroxynonanoic acid (668421-68-9)

Guidance literature:

Multi-step reaction with 14 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

13.1: aq. CAN / acetonitrile / 0.12 h / 0 °C

14.1: H₂; Et₃N / Pd/C / methanol / 20 h / 20 °C

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

DOI:10.1002/chem.200500417

upstream raw materials:

(3R,4S,7S,8R)-3-benzyloxy-9-(t-butyldiphenylsiloxy)-7-hydroxy-4,8-dimethyl-cis-5-nonenoic acid

(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

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