(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(3R,4S)-3-(2-methyl-allyl)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

Base Information

Chemical Name:(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(3R,4S)-3-(2-methyl-allyl)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester
CAS No.:217175-24-1
Molecular Formula:C₄₅H₅₂N₂O₇SSi
Molecular Weight:793.069
Hs Code.:

(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(3R,4S)-3-(2-methyl-allyl)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

Synonyms:(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(3R,4S)-3-(2-methyl-allyl)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

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Chemical Property of (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(3R,4S)-3-(2-methyl-allyl)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

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Technology Process of (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(3R,4S)-3-(2-methyl-allyl)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

There total 12 articles about (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(3R,4S)-3-(2-methyl-allyl)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic 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: 79.0%

: 1458-98-6
2-methyl-3-bromo-1-propene

: 217175-23-0
(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(S)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

: 217175-24-1
(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(3R,4S)-3-(2-methyl-allyl)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

Guidance literature:: (4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(S)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

2-methyl-3-bromo-1-propene; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; at -78 ℃;
DOI:10.1021/jo9817117

Reference yield:

: 18303-04-3
N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide

: 217175-24-1
(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(3R,4S)-3-(2-methyl-allyl)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: Ph₃P; DEAD / tetrahydrofuran

2.1: n-BuLi / diethyl ether

3.1: H₂ / Pd/CaCO₃/Pb / toluene

4.1: lithium hexamethyldisilazane / tetrahydrofuran; 1,2-dimethoxy-ethane / -78 °C

4.2: 71 percent / tetrahydrofuran; 1,2-dimethoxy-ethane / -78 °C

5.1: 69 percent / dimethylsulfoxide / 180 °C

6.1: 91 percent / Me₃Al / toluene

7.1: LHMDS / tetrahydrofuran / -78 °C

7.2: 79 percent / N,N-dimethylpropylene urea / tetrahydrofuran / -78 °C

With n-butyllithium; hydrogen; trimethylaluminum; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; Lindlar's catalyst; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dimethyl sulfoxide; toluene; 1.1: Alkylation / 2.1: Acylation / 3.1: Catalytic hydrogenation / 4.1: Metallation / 4.2: Michael addition / 5.1: Elimination / 6.1: Cyclization / 7.1: Metallation / 7.2: Alkylation;
DOI:10.1021/jo9817117

Reference yield:

: 101924-53-2
diethyl (2S,3R)-2-azido-3-hydroxysuccinate

: 217175-24-1
(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-[(3R,4S)-3-(2-methyl-allyl)-2-oxo-1-(toluene-4-sulfonyl)-piperidin-4-yl]-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 54 percent / BH₃*Me₂S; NaBH₄ / tetrahydrofuran

2.1: 82 percent / imidazole / tetrahydrofuran

3.1: H₂ / Pd/C / ethyl acetate

4.1: CH₂Cl₂

5.1: lithium hexamethyldisilazane / tetrahydrofuran; 1,2-dimethoxy-ethane / -78 °C

5.2: 71 percent / tetrahydrofuran; 1,2-dimethoxy-ethane / -78 °C

6.1: 69 percent / dimethylsulfoxide / 180 °C

7.1: 91 percent / Me₃Al / toluene

8.1: LHMDS / tetrahydrofuran / -78 °C

8.2: 79 percent / N,N-dimethylpropylene urea / tetrahydrofuran / -78 °C

With 1H-imidazole; sodium tetrahydroborate; dimethylsulfide borane complex; hydrogen; trimethylaluminum; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; 1.1: Reduction / 2.1: silylation / 3.1: Catalytic hydrogenation / 4.1: Cyclization / 5.1: Metallation / 5.2: Michael addition / 6.1: Elimination / 7.1: Cyclization / 8.1: Metallation / 8.2: Alkylation;
DOI:10.1021/jo9817117