(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-butyric acid ethyl ester

Base Information

Chemical Name:(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-butyric acid ethyl ester
CAS No.:866343-48-8
Molecular Formula:C₂₃H₃₈O₅Si
Molecular Weight:422.637
Hs Code.:

Synonyms:(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-butyric acid ethyl ester

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Chemical Property of (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-butyric acid ethyl ester

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Technology Process of (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-butyric acid ethyl ester

There total 5 articles about (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-butyric acid ethyl ester 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: 94.0%

: 866343-55-7
ethyl (2S,3R)-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]-2-hydroxybutanoate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 866343-48-8
(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-butyric acid ethyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 60 ℃;
DOI:10.1002/chem.200500282

Reference yield:

: 39806-16-1
ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate

: 866343-48-8
(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-butyric acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1,4-bis-(9-O-dihydroquinidinyl)phthalazine; K₃[Fe(CN)6]; K₂OsO₄*2H₂O / K₂CO₃; CH₃SO₂NH₂ / 2-methyl-propan-2-ol / 0 °C

1.2: 8.732 g / p-TsOH*H₂O / acetone / 20 °C

2.1: 72 percent / Me₃SiCl / diethyl ether; hexane / 6 h / -78 °C

3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

3.2: 59 percent / oxodiperoxymolybdenum(pyridine)-hexamethylphosphorictriamide / tetrahydrofuran / 3 h / -78 °C

4.1: 94 percent / imidazole / dimethylformamide / 60 °C

With 1H-imidazole; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; potassium osmate(VI); chloro-trimethyl-silane; potassium hexacyanoferrate(III); lithium diisopropyl amide; methanesulfonamide; potassium carbonate; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1002/chem.200500282

Reference yield:

: 866343-47-7
ethyl (3R)-2-acetoxy-3-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]butanoate

: 866343-48-8
(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-((4R,5R)-2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-butyric acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: NaOEt / ethanol / 20 °C

2: 94 percent / imidazole / dimethylformamide / 60 °C

With 1H-imidazole; sodium ethanolate; In ethanol; N,N-dimethyl-formamide;
DOI:10.1002/chem.200500282