(3S,4S,5S)-tert-butyl 3-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)(2-oxiranyl))-3-hydroxypropanoate

Base Information

Chemical Name:(3S,4S,5S)-tert-butyl 3-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)(2-oxiranyl))-3-hydroxypropanoate
CAS No.:172691-21-3
Molecular Formula:C₂₈H₄₀O₅Si
Molecular Weight:484.708
Hs Code.:

Synonyms:(3S,4S,5S)-tert-butyl 3-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)(2-oxiranyl))-3-hydroxypropanoate

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Chemical Property of (3S,4S,5S)-tert-butyl 3-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)(2-oxiranyl))-3-hydroxypropanoate

Chemical Property:

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Technology Process of (3S,4S,5S)-tert-butyl 3-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)(2-oxiranyl))-3-hydroxypropanoate

There total 7 articles about (3S,4S,5S)-tert-butyl 3-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)(2-oxiranyl))-3-hydroxypropanoate 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:

: 540-88-5
acetic acid tert-butyl ester

: 256494-34-5
(2R,3S)-3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)oxirane-2-carbaldehyde

: 172691-21-3
(3S,4S,5S)-tert-butyl 3-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)(2-oxiranyl))-3-hydroxypropanoate

: (3R,4S,5S)-tert-butyl 3-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)(2-oxiranyl))-3-hydroxypropanoate

Guidance literature:: acetic acid tert-butyl ester; With lithium diisopropyl amide; In diethyl ether; hexane; at -78 ℃; for 1h;

(2R,3S)-3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)oxirane-2-carbaldehyde; In diethyl ether; hexane; at -78 - -22 ℃;
DOI:10.1016/S0040-4020(99)00844-3

Reference yield:

: 127793-62-8
4-((tert-butyldiphenylsilyl)oxy)butanal

: 172691-21-3
(3S,4S,5S)-tert-butyl 3-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)(2-oxiranyl))-3-hydroxypropanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / toluene / 2.5 h / -78 °C

1.2: 8.44 g / toluene / 3.75 h / -78 °C

2.1: Dibal / toluene / 1 h / -78 °C

3.1: 91 percent / (+)-DET; titanium isopropoxide; tert-butylhydroperoxide / CH₂Cl₂ / 1 h / -20 °C

4.1: 84 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / 1 h

5.1: lithium diisopropylamide / hexane; diethyl ether / 1 h / -78 °C

5.2: hexane; diethyl ether / -78 - -22 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In diethyl ether; hexane; dichloromethane; toluene; 1.1: Metallation / 1.2: Condensation / 2.1: Reduction / 3.1: Epoxidation / 4.1: Oxidation / 5.1: deprotonation / 5.2: Condensation;
DOI:10.1016/S0040-4020(99)00844-3

Reference yield:

: 130372-07-5
4-(tret-butyldiphenylsilyloxy)butan-1-ol

: 172691-21-3
(3S,4S,5S)-tert-butyl 3-(3-(3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)propyl)(2-oxiranyl))-3-hydroxypropanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 85 percent / SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 1 h

2.1: n-BuLi / toluene / 2.5 h / -78 °C

2.2: 8.44 g / toluene / 3.75 h / -78 °C

3.1: Dibal / toluene / 1 h / -78 °C

4.1: 91 percent / (+)-DET; titanium isopropoxide; tert-butylhydroperoxide / CH₂Cl₂ / 1 h / -20 °C

5.1: 84 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / 1 h

6.1: lithium diisopropylamide / hexane; diethyl ether / 1 h / -78 °C

6.2: hexane; diethyl ether / -78 - -22 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In diethyl ether; hexane; dichloromethane; toluene; 1.1: Oxidation / 2.1: Metallation / 2.2: Condensation / 3.1: Reduction / 4.1: Epoxidation / 5.1: Oxidation / 6.1: deprotonation / 6.2: Condensation;
DOI:10.1016/S0040-4020(99)00844-3