<3S,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-(4-pentenyl)isoxazolidine

Base Information

Chemical Name:<3S,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-(4-pentenyl)isoxazolidine
CAS No.:131447-04-6
Molecular Formula:C₂₇H₃₇NO₂
Molecular Weight:407.596
Hs Code.:

Synonyms:<3S,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-(4-pentenyl)isoxazolidine

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Chemical Property of <3S,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-(4-pentenyl)isoxazolidine

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Technology Process of <3S,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-(4-pentenyl)isoxazolidine

There total 11 articles about <3S,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-(4-pentenyl)isoxazolidine 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: 86.0%

: 7103-09-5
4-but-1-enylmagnesium bromide

: 131447-03-5
<3R,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-(iodomethyl)isoxazolidine

: 131447-04-6
<3S,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-(4-pentenyl)isoxazolidine

Guidance literature:: With thien-2-yl(cyano)copper lithium; In tetrahydrofuran; -78 deg C to r.t.;
DOI:10.1016/S0040-4039(00)97807-9

Reference yield:

: 84379-53-3
2-O-benzyl-3,4-O-isopropylidene-L-threitol

: 131447-04-6
<3S,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-(4-pentenyl)isoxazolidine

Guidance literature:: Multi-step reaction with 10 steps

1: 97 percent / N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h

2: 87 percent / Li₂CuCl₄ / tetrahydrofuran / 1) -78 deg C, 1.5 h, 2) room temp., 65 h

3: 98 percent / 6N HCl / methanol / 1 h / 55 °C

4: 1.5 h / 70 °C

5: acetic anhydride / 1 h / Heating

6: 57 percent / toluene / 14 h / Heating

7: 96 percent / LiAlH₄ / diethyl ether / 14 h / Ambient temperature

8: 97 percent / N,N-dimethylaminopyridine, diisopropylethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

9: 80 percent / NaI / butan-2-one / 5.5 h / 75 °C

10: 1) (2-thienyl)Cu(CN)Li / 1) THF, a) -78 deg C, 15 min, b) 0 deg C, 1.5 h, 2) a) -78 deg C, 15 min, b) 0 deg C, 1.5 h, c) room temp., 18 h

With hydrogenchloride; dmap; lithium aluminium tetrahydride; dilithium tetrachlorocuprate; acetic anhydride; thien-2-yl(cyano)copper lithium; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; butanone;
DOI:10.1016/S0040-4020(01)80881-4

Reference yield:

: 131446-96-3
(S)-2-(benzyloxy)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate

: 131447-04-6
<3S,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-(4-pentenyl)isoxazolidine

Guidance literature:: Multi-step reaction with 9 steps

1: 87 percent / Li₂CuCl₄ / tetrahydrofuran / 1) -78 deg C, 1.5 h, 2) room temp., 65 h

2: 98 percent / 6N HCl / methanol / 1 h / 55 °C

3: 1.5 h / 70 °C

4: acetic anhydride / 1 h / Heating

5: 57 percent / toluene / 14 h / Heating

6: 96 percent / LiAlH₄ / diethyl ether / 14 h / Ambient temperature

7: 97 percent / N,N-dimethylaminopyridine, diisopropylethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

8: 80 percent / NaI / butan-2-one / 5.5 h / 75 °C

9: 1) (2-thienyl)Cu(CN)Li / 1) THF, a) -78 deg C, 15 min, b) 0 deg C, 1.5 h, 2) a) -78 deg C, 15 min, b) 0 deg C, 1.5 h, c) room temp., 18 h

With hydrogenchloride; dmap; lithium aluminium tetrahydride; dilithium tetrachlorocuprate; acetic anhydride; thien-2-yl(cyano)copper lithium; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; butanone;
DOI:10.1016/S0040-4020(01)80881-4