(3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonane-1,3-diol

Base Information

Chemical Name:(3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonane-1,3-diol
CAS No.:1353654-11-1
Molecular Formula:C₂₁H₃₈O₃Si
Molecular Weight:366.616
Hs Code.:

Synonyms:(3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonane-1,3-diol

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Chemical Property of (3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonane-1,3-diol

Chemical Property:

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Technology Process of (3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonane-1,3-diol

There total 10 articles about (3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonane-1,3-diol 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: 90.0%

: 1353654-10-0
[(2R,3R)-3-((2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-6-phenylhexyl)oxiran-2-yl]methanol

: 1353654-11-1
(3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonane-1,3-diol

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; toluene; at 0 ℃; regioselective reaction;
DOI:10.1055/s-0030-1260214

Reference yield:

: [(2R,3R)-3-(4-phenylbutyl)oxiran-2-yl]methanol

: 1353654-11-1
(3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonane-1,3-diol

Guidance literature:: Multi-step reaction with 9 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

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

: 1353654-11-1
(3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-9-phenylnonane-1,3-diol

Guidance literature:: Multi-step reaction with 10 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

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