4β,5α,4-<(E)-3-Hydroxy-1-octenyl>-5-(phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole

Base Information

Chemical Name:4β,5α,4-<(E)-3-Hydroxy-1-octenyl>-5-(phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole
CAS No.:89923-29-5
Molecular Formula:C₂₁H₂₉NO₃
Molecular Weight:343.466
Hs Code.:

4β,5α,4-<(E)-3-Hydroxy-1-octenyl>-5-(phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopent<c>isoxazole

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 4β,5α,4-<(E)-3-Hydroxy-1-octenyl>-5-(phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole

Chemical Property:

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Technology Process of 4β,5α,4-<(E)-3-Hydroxy-1-octenyl>-5-(phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole

There total 13 articles about 4β,5α,4-<(E)-3-Hydroxy-1-octenyl>-5-(phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole 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:

: 89923-23-9
4β,5α-5-Hydroxy-4-(hydroxymethyl)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole

: 89923-29-5
4β,5α,4-<(E)-3-Hydroxy-1-octenyl>-5-(phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole

Guidance literature:: Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 3 h

2: 1.) NaH / 2.) n-Bu₄NI / 1.) THF, 15 h; 2.) 3 h

3: n-Bu₄NF / tetrahydrofuran / 1 h

4: 84 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 2.) room temp.

5: 1.) NaH / 1.) DME, 1 h; 2.) 0 deg C, 5 min

6: NaBH₄, CeCl₃*6H₂O / methanol / 0.08 h

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00187a001

Reference yield:

: 89923-24-0
(3aS,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3a,4,5,6-tetrahydro-3H-cyclopenta[c]isoxazol-5-ol

: 89923-29-5
4β,5α,4-<(E)-3-Hydroxy-1-octenyl>-5-(phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH / 2.) n-Bu₄NI / 1.) THF, 15 h; 2.) 3 h

2: n-Bu₄NF / tetrahydrofuran / 1 h

3: 84 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 2.) room temp.

4: 1.) NaH / 1.) DME, 1 h; 2.) 0 deg C, 5 min

5: NaBH₄, CeCl₃*6H₂O / methanol / 0.08 h

With sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo00187a001

Reference yield:

: 89923-06-8,89923-07-9
Ethyl 2-Ethenyl-3-hydroxy-5-(phenylmethoxy)pentanoate

: 89923-29-5
4β,5α,4-<(E)-3-Hydroxy-1-octenyl>-5-(phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole

Guidance literature:: Multi-step reaction with 13 steps

1: 13.4 g / LAH / diethyl ether

2: Amberlyst-15 / 24 h

3: 37 percent / Na / NH₃ / ethanol / tetrahydrofuran / 0.08 h / -78 °C

4: oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C; 2.) 5 min room temp.

5: 66 percent / H₂NOH*HCl, pyridime / 1 h

6: 75 percent / aq.NaOCl / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) room temp., 18 h;

7: Amberlyst-15 / methanol / 1 h / Ambient temperature

8: imidazole / dimethylformamide / 3 h

9: 1.) NaH / 2.) n-Bu₄NI / 1.) THF, 15 h; 2.) 3 h

10: n-Bu₄NF / tetrahydrofuran / 1 h

11: 84 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 2.) room temp.

12: 1.) NaH / 1.) DME, 1 h; 2.) 0 deg C, 5 min

13: NaBH₄, CeCl₃*6H₂O / methanol / 0.08 h

With pyridine; 1H-imidazole; sodium hypochlorite; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; oxalyl dichloride; ethanol; hydroxylamine hydrochloride; ammonia; sodium; sodium hydride; dimethyl sulfoxide; triethylamine; amberlyst-15; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00187a001