(3S,5R)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonyl pivalate

Base Information

• Chemical Name: (3S,5R)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonyl pivalate
• CAS No.: 1353654-12-2
• Molecular Formula: C₃₂H₆₀O₄Si₂
• Molecular Weight: 564.997
• Mol file: 1353654-12-2.mol

Synonyms:(3S,5R)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonyl pivalate

Chemical Property of (3S,5R)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonyl pivalate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonyl pivalate

There total 13 articles about (3S,5R)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonyl pivalate 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: 95.0%

(3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-9-phenylnonyl pivalate (1353654-16-6) + tert-butyldimethylsilyl chloride (18162-48-6) → (3S,5R)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonyl pivalate (1353654-12-2)

Guidance literature:

(3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-9-phenylnonyl pivalate; tert-butyldimethylsilyl chloride; With 1H-imidazole; In dichloromethane; at 0 ℃; for 0.0833333h;

With dmap; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1055/s-0030-1260214

Reference yield:

[(2R,3R)-3-(4-phenylbutyl)oxiran-2-yl]methanol → (3S,5R)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonyl pivalate (1353654-12-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 3 h / 0 °C

2.1: pyridine / dichloromethane / 0 - 20 °C

3.1: 1H-imidazole / dichloromethane / 0.08 h / 0 °C

3.2: 1 h / 20 °C

4.1: diisobutylaluminium hydride / tetrahydrofuran / 0.5 h / -78 °C

5.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2.75 h / -78 °C

6.1: benzene / 2 h / Reflux

7.1: lithium aluminium tetrahydride; aluminum (III) chloride / tetrahydrofuran / 3 h / 0 - 20 °C

8.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

8.2: 12 h / -20 °C

9.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0 °C

10.1: pyridine / dichloromethane / 0 - 20 °C

11.1: 1H-imidazole / dichloromethane / 0.08 h / 0 °C

11.2: 1 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; aluminum (III) chloride; lithium aluminium tetrahydride; oxalyl dichloride; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; toluene; benzene; 5.1: Swern oxidation / 6.1: Wittig reaction / 8.1: Sharpless asymmetric epoxidation / 8.2: Sharpless asymmetric epoxidation;

DOI:10.1055/s-0030-1260214

Reference yield:

(E)-7-phenylhept-2-en-1-ol → (3S,5R)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonyl pivalate (1353654-12-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

1.2: 12 h / -20 °C

2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 3 h / 0 °C

3.1: pyridine / dichloromethane / 0 - 20 °C

4.1: 1H-imidazole / dichloromethane / 0.08 h / 0 °C

4.2: 1 h / 20 °C

5.1: diisobutylaluminium hydride / tetrahydrofuran / 0.5 h / -78 °C

6.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 2.75 h / -78 °C

7.1: benzene / 2 h / Reflux

8.1: lithium aluminium tetrahydride; aluminum (III) chloride / tetrahydrofuran / 3 h / 0 - 20 °C

9.1: titanium(IV) isopropylate; diethyl (2S,3S)-tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

9.2: 12 h / -20 °C

10.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0 °C

11.1: pyridine / dichloromethane / 0 - 20 °C

12.1: 1H-imidazole / dichloromethane / 0.08 h / 0 °C

12.2: 1 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; aluminum (III) chloride; lithium aluminium tetrahydride; oxalyl dichloride; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; toluene; benzene; 1.1: Sharpless asymmetric epoxidation / 1.2: Sharpless asymmetric epoxidation / 6.1: Swern oxidation / 7.1: Wittig reaction / 9.1: Sharpless asymmetric epoxidation / 9.2: Sharpless asymmetric epoxidation;

DOI:10.1055/s-0030-1260214

upstream raw materials:

(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-7-phenylheptan-1-ol

(3R)-3-[tert-butyl(dimethyl)silyloxy]-7-phenylheptanal

ethyl (2E)-7-phenylhept-2-enoate

[(2R,3R)-3-((2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-6-phenylhexyl)oxiran-2-yl]methanol

Downstream raw materials:

(3S,5R)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonan-1-ol

methyl (2Z,5S,7R)-5,7-bis{[tert-butyl(dimethyl)silyl]oxy}-11-phenylundec-2-enoate

C₂₇H₅₀O₃Si₂

(6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one