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

Base Information

• Chemical Name: (3S,4S,7S,8R)-3-benzyloxy-9-hydroxy-4,8-dimethylnonan-7-olide
• CAS No.: 861701-99-7
• Molecular Formula: C₁₈H₂₆O₄
• Molecular Weight: 306.402
• Mol file: 861701-99-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 34 articles about (3S,4S,7S,8R)-3-benzyloxy-9-hydroxy-4,8-dimethylnonan-7-olide 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: 86.0%

(3R,4S,7S,8R)-3-benzyloxy-9-(tert-butyldiphenylsiloxy)-4,8-dimethylnonan-7-olide (668421-67-8) → (3S,4S,7S,8R)-3-benzyloxy-9-hydroxy-4,8-dimethylnonan-7-olide (861701-99-7)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetlet.2003.10.213

Reference yield:

methyl 3-hydroxy-4-(triisopropylsiloxy)-2-methylbutanoate → (3S,4S,7S,8R)-3-benzyloxy-9-hydroxy-4,8-dimethylnonan-7-olide (861701-99-7)

Guidance literature:

Multi-step reaction with 15 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

14.1: 2-methyl-6-nitrobenzoic anhydride; DMAPO; Et₃N / CH₂Cl₂ / 13 h / 20 °C

15.1: TBAF; AcOH / tetrahydrofuran / 13 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; 2-methyl-6-nitrobenzoic anhydride; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; acetic acid; 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 → (3S,4S,7S,8R)-3-benzyloxy-9-hydroxy-4,8-dimethylnonan-7-olide (861701-99-7)

Guidance literature:

Multi-step reaction with 16 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

15.1: 2-methyl-6-nitrobenzoic anhydride; DMAPO; Et₃N / CH₂Cl₂ / 13 h / 20 °C

16.1: TBAF; AcOH / tetrahydrofuran / 13 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; 2-methyl-6-nitrobenzoic anhydride; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; acetic acid; 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-(tert-butyldiphenylsiloxy)-4,8-dimethylnonan-7-olide

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

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

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

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