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

Base Information

Chemical Name:(3R,4S,5R)-tert-butyl 3-(3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)(2-oxiranyl))-3-hydroxypropanoate
CAS No.:256494-38-9
Molecular Formula:C₂₇H₃₈O₅Si
Molecular Weight:470.681
Hs Code.:

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

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

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

There total 6 articles about (3R,4S,5R)-tert-butyl 3-(3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)(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:

: 88158-68-3
4-(tert-butyldiphenylsilyloxy)-1-butyne

: 256494-38-9
(3R,4S,5R)-tert-butyl 3-(3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)(2-oxiranyl))-3-hydroxypropanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: BuLi / diethyl ether / -78 - 20 °C

1.2: 72 percent / diethyl ether / -78 - 20 °C

2.1: H₂ / palladium/C/BaSO₄ / methanol; quinoline / 2 h / -20 °C

3.1: 88 percent / (+)-DIPT; titanium isopropoxide; tert-butylhydroperoxide / CH₂Cl₂ / 18.5 h / -20 °C

4.1: 78 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / 1 h

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

5.2: 0.19 g / hexane; diethyl ether / -78 - 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; hydrogen; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; Pd-BaSO₄; In quinoline; methanol; diethyl ether; hexane; dichloromethane; 1.1: Metallation / 1.2: Addition / 2.1: Hydrogenation / 3.1: Epoxidation / 4.1: Oxidation / 5.1: deprotonation / 5.2: Condensation;
DOI:10.1016/S0040-4020(99)00844-3

Reference yield:

: 88159-03-9
5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-yn-1-ol

: 256494-38-9
(3R,4S,5R)-tert-butyl 3-(3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)(2-oxiranyl))-3-hydroxypropanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: H₂ / palladium/C/BaSO₄ / methanol; quinoline / 2 h / -20 °C

2.1: 88 percent / (+)-DIPT; titanium isopropoxide; tert-butylhydroperoxide / CH₂Cl₂ / 18.5 h / -20 °C

3.1: 78 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / 1 h

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

4.2: 0.19 g / hexane; diethyl ether / -78 - 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; hydrogen; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; Pd-BaSO₄; In quinoline; methanol; diethyl ether; hexane; dichloromethane; 1.1: Hydrogenation / 2.1: Epoxidation / 3.1: Oxidation / 4.1: deprotonation / 4.2: Condensation;
DOI:10.1016/S0040-4020(99)00844-3

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 256494-38-9
(3R,4S,5R)-tert-butyl 3-(3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)(2-oxiranyl))-3-hydroxypropanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 100 percent / imidazole / dimethylformamide / 5 h / 20 °C

2.1: BuLi / diethyl ether / -78 - 20 °C

2.2: 72 percent / diethyl ether / -78 - 20 °C

3.1: H₂ / palladium/C/BaSO₄ / methanol; quinoline / 2 h / -20 °C

4.1: 88 percent / (+)-DIPT; titanium isopropoxide; tert-butylhydroperoxide / CH₂Cl₂ / 18.5 h / -20 °C

5.1: 78 percent / SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / 1 h

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

6.2: 0.19 g / hexane; diethyl ether / -78 - 25 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; hydrogen; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; Pd-BaSO₄; In quinoline; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Metallation / 2.2: Addition / 3.1: Hydrogenation / 4.1: Epoxidation / 5.1: Oxidation / 6.1: deprotonation / 6.2: Condensation;
DOI:10.1016/S0040-4020(99)00844-3