(R)-3-((S)-3-((benzyloxy)methyl)hex-5-enoyl)-4-isopropyl-1,3-oxazolidin-2-one

Base Information

Chemical Name:(R)-3-((S)-3-((benzyloxy)methyl)hex-5-enoyl)-4-isopropyl-1,3-oxazolidin-2-one
CAS No.:1347738-34-4
Molecular Formula:C₂₀H₂₇NO₄
Molecular Weight:345.439
Hs Code.:

Synonyms:

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Chemical Property of (R)-3-((S)-3-((benzyloxy)methyl)hex-5-enoyl)-4-isopropyl-1,3-oxazolidin-2-one

Chemical Property:

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Technology Process of (R)-3-((S)-3-((benzyloxy)methyl)hex-5-enoyl)-4-isopropyl-1,3-oxazolidin-2-one

There total 1 articles about (R)-3-((S)-3-((benzyloxy)methyl)hex-5-enoyl)-4-isopropyl-1,3-oxazolidin-2-one 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: 39.0%

: C₁₇H₂₁NO₄

: 24850-33-7
allyltributylstanane

: 1347738-34-4
(R)-3-((S)-3-((benzyloxy)methyl)hex-5-enoyl)-4-isopropyl-1,3-oxazolidin-2-one

Guidance literature:: C₁₇H₂₁NO₄; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere;

allyltributylstanane; In dichloromethane; at -78 ℃; for 3h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/jo201988m

Reference yield:

: 1347738-34-4
(R)-3-((S)-3-((benzyloxy)methyl)hex-5-enoyl)-4-isopropyl-1,3-oxazolidin-2-one

: 74-88-4
methyl iodide

: 1360801-31-5
(R)-3-((2R,3S)-3-((benzyloxy)methyl)-2-methylhex-5-enoyl)-4-isopropyl-1,3-oxazolidin-2-one

: (R)-3-((2S,3S)-3-((benzyloxy)methyl)-2-methylhex-5-enoyl)-4-isopropyl-1,3-oxazolidin-2-one

Guidance literature:: (R)-3-((S)-3-((benzyloxy)methyl)hex-5-enoyl)-4-isopropyl-1,3-oxazolidin-2-one; With lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - -25 ℃; for 1h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at -25 ℃; for 6h; optical yield given as %de; Inert atmosphere;
DOI:10.1021/jo201988m

Reference yield:

: 1347738-34-4
(R)-3-((S)-3-((benzyloxy)methyl)hex-5-enoyl)-4-isopropyl-1,3-oxazolidin-2-one

: 1182098-75-4
C₃₉H₅₀O₇Si

Guidance literature:: Multi-step reaction with 16 steps

1.1: lithium chloride; lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 - -25 °C / Inert atmosphere

1.2: 6 h / -25 °C / Inert atmosphere

2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 20 °C

3.1: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide / 18 h / 0 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: 4 h / -78 °C / Inert atmosphere

5.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 36 h / 20 °C

6.1: sodium periodate / 1,4-dioxane; water; tert-butyl alcohol / 2 h / 20 °C

7.1: dimethylsulfide borane complex / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

8.1: 1H-imidazole; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

9.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C

9.2: pH 4

10.1: toluene-4-sulfonic acid / toluene / 2 h / 20 °C

11.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere

11.2: 3 h / -78 °C / Inert atmosphere

12.1: tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

13.1: 1H-imidazole / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

14.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

15.1: boron trifluoride diethyl etherate / dichloromethane / 0.25 h / -78 - 0 °C / Inert atmosphere

15.2: 0.5 h / -78 °C / Inert atmosphere

16.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol; water; ethyl acetate / 4 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; hydrogenchloride; dmap; sodium periodate; osmium(VIII) oxide; n-butyllithium; dimethylsulfide borane complex; palladium 10% on activated carbon; boron trifluoride diethyl etherate; water; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; HATU; lithium chloride; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/jo201988m