(4S,5S)-5-[(S)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-pent-4-enyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(4S,5S)-5-[(S)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-pent-4-enyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:134916-01-1
Molecular Formula:C₃₃H₄₈N₂O₆
Molecular Weight:568.754
Hs Code.:

(4S,5S)-5-[(S)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-pent-4-enyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (4S,5S)-5-[(S)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-pent-4-enyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (4S,5S)-5-[(S)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-pent-4-enyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 2 articles about (4S,5S)-5-[(S)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-pent-4-enyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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:

: [(2S,3S)-3-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-1-cyclohexylmethyl-2-hydroxy-hept-6-enyl]-carbamic acid tert-butyl ester

: 77-76-9
2,2-dimethoxy-propane

: 134916-01-1
(4R,5S)-5-[(S)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-pent-4-enyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 134916-01-1
(4S,5S)-5-[(S)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-pent-4-enyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; Yield given. Yields of byproduct given;
DOI:10.1016/S0040-4039(00)74351-6

Reference yield:

: [(2S,3S)-3-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-1-cyclohexylmethyl-2-hydroxy-hept-6-enyl]-carbamic acid tert-butyl ester

: 77-76-9
2,2-dimethoxy-propane

: 134916-01-1
(4R,5S)-5-[(S)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-pent-4-enyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 134916-01-1
(4S,5S)-5-[(S)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-pent-4-enyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; Yield given. Yields of byproduct given;
DOI:10.1016/S0040-4039(00)74351-6

Reference yield:

: 134916-01-1
(4S,5S)-5-[(S)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-pent-4-enyl]-4-cyclohexylmethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 134916-09-9
[(3S,12S,13S,14S)-14-Cyclohexylmethyl-13-hydroxy-12-((S)-2-methyl-butylcarbamoyl)-2,6-dioxo-1,7-diaza-cyclotetradec-3-yl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: LiOH, H₂O₂ / tetrahydrofuran; H₂O

2: EDC, HOBT

3: 1) BH₃*THF 2) 1N NaOH, H₂O₂

4: Et₃N / CH₂Cl₂ / 0 °C

5: LiN₃ / dimethylformamide

6: 1,3-propanedithiol, Et₃N

7: Et₃N / CH₂Cl₂

8: HCl / methanol

9: Et₃N, EDC, HOBT

10: H₂ / Pd/C / methanol

11: diphenylphosphoryl azide / dimethylformamide / 120 h / 0 - 4 °C

With 1.3-propanedithiol; hydrogenchloride; lithium hydroxide; sodium hydroxide; lithium azide; borane-THF; diphenylphosphoranyl azide; hydrogen; dihydrogen peroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)74351-6