methyl α,5-dimethyl-4-(phenylmethoxy)-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate

Base Information

Chemical Name:methyl α,5-dimethyl-4-(phenylmethoxy)-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate
CAS No.:82043-29-6
Molecular Formula:C₂₄H₃₄O₅
Molecular Weight:402.531
Hs Code.:

Synonyms:methyl α,5-dimethyl-4-(phenylmethoxy)-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate

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Chemical Property of methyl α,5-dimethyl-4-(phenylmethoxy)-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate

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Technology Process of methyl α,5-dimethyl-4-(phenylmethoxy)-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate

There total 1 articles about methyl α,5-dimethyl-4-(phenylmethoxy)-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate 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: 87.0%

: 100-39-0
benzyl bromide

: 82041-93-8
methyl α,5-dimethyl-4-hydroxy-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate

: 82043-29-6
methyl α,5-dimethyl-4-(phenylmethoxy)-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1.) 0 deg C, 30 min, 2.) room temperature, 1 h, 3.) 50 deg C, 12 h;
DOI:10.1021/ja00379a030

Reference yield:

: 82043-29-6
methyl α,5-dimethyl-4-(phenylmethoxy)-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate

: 68241-55-4
(1aα,4β,4aβ,7α,7aα,7bα)-3,4,4a,7,7a,7b-hexahydro-4,7a-dimethyl-7-(phenylmethoxy)azuleno<4,5-b>oxiren-2(1aH)-one

Guidance literature:: Multi-step reaction with 18 steps

1: p-toluenesulfonic acid / methanol / 2 h / Ambient temperature

2: 89 percent / 10percent aq. KOH / methanol / 21 h / 55 °C

3: 64 percent / p-toluenesulfonyl chloride, DBU / toluene / 1.) 0 deg C, 15 min, 2.) ambient temperature, 1 h

4: 92 percent / DBU / toluene / 3 h / Heating

5: i-Bu₂AlH / toluene / 0.5 h / -78 °C

6: benzene / 1 h / Ambient temperature

7: 85 percent / Collins reagent / CH₂Cl₂ / 0.5 h / 0 °C

8: 99 percent / 10percent aq. HCl / tetrahydrofuran / 12 h / Ambient temperature

9: 1.5percent KOH / methanol / 8 h / Ambient temperature

10: p-toluenesulfonic acid / CH₂Cl₂ / 1 h / 0 °C

11: 365 mg / NaBH₄ / methanol / 1.) 0 deg C, 2 h, 2.) room temperature, 3 h

12: 96 percent / pyridine / 2 h / Ambient temperature

13: 344 mg / p-toluenesulfonic acid / methanol / 1.) 0 deg c, 1 h, 2.) room temperature, 2 h

14: 342 mg / Jones reagent / acetone / 0.25 h / 0 °C

15: DBU / benzene / 0.25 h / Ambient temperature

16: LiAlH₄

17: MCPBA / CH₂Cl₂

18: Collins

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; jones reagent; Collins oxidation agent; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetone; toluene; benzene;
DOI:10.1021/ja00379a030

Reference yield:

: 82043-29-6
methyl α,5-dimethyl-4-(phenylmethoxy)-5-<1-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-2-cyclopentene-1-acetate

: 71686-37-8,73407-83-7,73407-85-9
(3aβ,4β,4aα,5α,7aβ,8β,9aβ)-3a,4,4a,5,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-5-(phenylmethoxy)azuleno<6,5-b>furan-2(3H)-one

Guidance literature:: Multi-step reaction with 20 steps

1: p-toluenesulfonic acid / methanol / 2 h / Ambient temperature

2: 89 percent / 10percent aq. KOH / methanol / 21 h / 55 °C

3: 64 percent / p-toluenesulfonyl chloride, DBU / toluene / 1.) 0 deg C, 15 min, 2.) ambient temperature, 1 h

4: 92 percent / DBU / toluene / 3 h / Heating

5: i-Bu₂AlH / toluene / 0.5 h / -78 °C

6: benzene / 1 h / Ambient temperature

7: 85 percent / Collins reagent / CH₂Cl₂ / 0.5 h / 0 °C

8: 99 percent / 10percent aq. HCl / tetrahydrofuran / 12 h / Ambient temperature

9: 1.5percent KOH / methanol / 8 h / Ambient temperature

10: p-toluenesulfonic acid / CH₂Cl₂ / 1 h / 0 °C

11: 365 mg / NaBH₄ / methanol / 1.) 0 deg C, 2 h, 2.) room temperature, 3 h

12: 96 percent / pyridine / 2 h / Ambient temperature

13: 344 mg / p-toluenesulfonic acid / methanol / 1.) 0 deg c, 1 h, 2.) room temperature, 2 h

14: 342 mg / Jones reagent / acetone / 0.25 h / 0 °C

15: DBU / benzene / 0.25 h / Ambient temperature

16: LiAlH₄

17: MCPBA / CH₂Cl₂

18: Collins

19: 98 percent / NaBH₄ / ethanol / 1 h / 0 °C

20: 1.) diisopropylamine, n-BuLi, acetic acid / 1.) DME, hexane, -42 deg C, 10 min; 43 deg C, 90 min, 2.) 55 deg C, 20 h

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; jones reagent; Collins oxidation agent; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; acetone; toluene; benzene;
DOI:10.1021/ja00379a030