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

Base Information

• Chemical Name: (3R,4S,7S,8R)-3-benzyloxy-9-(t-butyldiphenylsiloxy)-7-hydroxy-4,8-dimethyl-cis-5-nonenoic acid
• CAS No.: 861700-68-7
• Molecular Formula: C₃₄H₄₄O₅Si
• Molecular Weight: 560.806
• Mol file: 861700-68-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 30 articles about (3R,4S,7S,8R)-3-benzyloxy-9-(t-butyldiphenylsiloxy)-7-hydroxy-4,8-dimethyl-cis-5-nonenoic acid 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: 81.0%

(3R,4S,7S,8R)-3-benzyloxy-9-(t-butyldiphenylsiloxy)-7-(p-methoxybenzyloxy)-4,8-dimethyl-cis-5-nonenoic acid (668421-79-2) → (3R,4S,7S,8R)-3-benzyloxy-9-(t-butyldiphenylsiloxy)-7-hydroxy-4,8-dimethyl-cis-5-nonenoic acid (861700-68-7)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; 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-(t-butyldiphenylsiloxy)-7-hydroxy-4,8-dimethyl-cis-5-nonenoic acid (861700-68-7)

Guidance literature:

Multi-step reaction with 12 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

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; 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-hydroxy-4,8-dimethyl-cis-5-nonenoic acid (861700-68-7)

Guidance literature:

Multi-step reaction with 13 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

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; 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:

(3R,4S,7S,8R)-3-benzyloxy-9-(t-butyldiphenylsiloxy)-7-(p-methoxybenzyloxy)-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

(3R,4S,7S,8R,13S)-3-benzyloxy-13-(t-butyldimethylsiloxy)-9-hydroxy-4,8,10,14-tetramethyl-(E)-10-pentadecen-7-olide