<4S,6R,6(1S)>-N-Benzyl-6-<1-(benzyloxy)pentyl>-4-<(4,4-ethylenedioxy)pentyl>-3,4,5,6-tetrahydro-1,3-oxazin-2-one

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Chemical Name:<4S,6R,6(1S)>-N-Benzyl-6-<1-(benzyloxy)pentyl>-4-<(4,4-ethylenedioxy)pentyl>-3,4,5,6-tetrahydro-1,3-oxazin-2-one
CAS No.:138890-26-3
Molecular Formula:C₃₀H₄₁NO₅
Molecular Weight:495.659
Hs Code.:

Synonyms:<4S,6R,6(1S)>-N-Benzyl-6-<1-(benzyloxy)pentyl>-4-<(4,4-ethylenedioxy)pentyl>-3,4,5,6-tetrahydro-1,3-oxazin-2-one

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Chemical Property of <4S,6R,6(1S)>-N-Benzyl-6-<1-(benzyloxy)pentyl>-4-<(4,4-ethylenedioxy)pentyl>-3,4,5,6-tetrahydro-1,3-oxazin-2-one

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Technology Process of <4S,6R,6(1S)>-N-Benzyl-6-<1-(benzyloxy)pentyl>-4-<(4,4-ethylenedioxy)pentyl>-3,4,5,6-tetrahydro-1,3-oxazin-2-one

There total 15 articles about <4S,6R,6(1S)>-N-Benzyl-6-<1-(benzyloxy)pentyl>-4-<(4,4-ethylenedioxy)pentyl>-3,4,5,6-tetrahydro-1,3-oxazin-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: 89.0%

: 138890-25-2
<4S,6R,6(1S)>-N-Benzyl-6-<1-(benzyloxy)pentyl>-4-(4-oxopentyl)-3,4,5,6-tetrahydro-1,3-oxazin-2-one

: 107-21-1
ethylene glycol

: 138890-26-3
<4S,6R,6(1S)>-N-Benzyl-6-<1-(benzyloxy)pentyl>-4-<(4,4-ethylenedioxy)pentyl>-3,4,5,6-tetrahydro-1,3-oxazin-2-one

Guidance literature:: With molecular sieve; toluene-4-sulfonic acid; In benzene; for 14h; Heating;
DOI:10.1016/S0040-4020(01)80881-4

Reference yield:

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

: 138890-26-3
<4S,6R,6(1S)>-N-Benzyl-6-<1-(benzyloxy)pentyl>-4-<(4,4-ethylenedioxy)pentyl>-3,4,5,6-tetrahydro-1,3-oxazin-2-one

Guidance literature:: Multi-step reaction with 14 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

11: 90 percent / Zn dust, AcOH / H₂O; tetrahydrofuran / 2.5 h / 60 °C

12: 1) sat. aq. Na₂CO₃, 2) 30percent aq. NH₃ / 1) CH₂Cl₂, room temp., 2 h, 2) ambient temp., 15 min

13: 89 percent / O₂ / PdCl₂, CuCl₂ / dimethylformamide; H₂O / 4 h / 50 °C

14: 89 percent / p-TsOH, molecular sieves / benzene / 14 h / Heating

With hydrogenchloride; dmap; ammonium hydroxide; lithium aluminium tetrahydride; molecular sieve; dilithium tetrachlorocuprate; oxygen; acetic anhydride; sodium carbonate; toluene-4-sulfonic acid; acetic acid; thien-2-yl(cyano)copper lithium; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc; copper dichloride; palladium dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; butanone; benzene;
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

: 138890-26-3
<4S,6R,6(1S)>-N-Benzyl-6-<1-(benzyloxy)pentyl>-4-<(4,4-ethylenedioxy)pentyl>-3,4,5,6-tetrahydro-1,3-oxazin-2-one

Guidance literature:: Multi-step reaction with 13 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

10: 90 percent / Zn dust, AcOH / H₂O; tetrahydrofuran / 2.5 h / 60 °C

11: 1) sat. aq. Na₂CO₃, 2) 30percent aq. NH₃ / 1) CH₂Cl₂, room temp., 2 h, 2) ambient temp., 15 min

12: 89 percent / O₂ / PdCl₂, CuCl₂ / dimethylformamide; H₂O / 4 h / 50 °C

13: 89 percent / p-TsOH, molecular sieves / benzene / 14 h / Heating

With hydrogenchloride; dmap; ammonium hydroxide; lithium aluminium tetrahydride; molecular sieve; dilithium tetrachlorocuprate; oxygen; acetic anhydride; sodium carbonate; toluene-4-sulfonic acid; acetic acid; thien-2-yl(cyano)copper lithium; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc; copper dichloride; palladium dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; butanone; benzene;
DOI:10.1016/S0040-4020(01)80881-4