2(5H)-Furanone, 4-[2-(octahydro-3,3,6,7-tetramethyl-11-methylene-1H,6H-naphtho[1,8a- d][1,3]dioxin-7-yl)-1-(phenylsulfonyl)ethyl]-

Base Information

• Chemical Name: 2(5H)-Furanone, 4-[2-(octahydro-3,3,6,7-tetramethyl-11-methylene-1H,6H-naphtho[1,8a- d][1,3]dioxin-7-yl)-1-(phenylsulfonyl)ethyl]-
• CAS No.: 87927-67-1
• Molecular Formula: C₂₉H₃₈O₆S
• Molecular Weight: 514.683
• Mol file: 87927-67-1.mol

Synonyms:

Chemical Property of 2(5H)-Furanone, 4-[2-(octahydro-3,3,6,7-tetramethyl-11-methylene-1H,6H-naphtho[1,8a- d][1,3]dioxin-7-yl)-1-(phenylsulfonyl)ethyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(5H)-Furanone, 4-[2-(octahydro-3,3,6,7-tetramethyl-11-methylene-1H,6H-naphtho[1,8a- d][1,3]dioxin-7-yl)-1-(phenylsulfonyl)ethyl]-

There total 19 articles about 2(5H)-Furanone, 4-[2-(octahydro-3,3,6,7-tetramethyl-11-methylene-1H,6H-naphtho[1,8a- d][1,3]dioxin-7-yl)-1-(phenylsulfonyl)ethyl]- 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:

2-methylbut-2-enal (497-03-0) → (6α,18-dihydroxy)acetonide-12-phenylsulphonylcleroda-4,13(14)-dieno-16,15-lactone (87927-67-1,111819-85-3,111820-77-0)

Guidance literature:

Multi-step reaction with 18 steps

1: 1.) hydroquinone; 2.) 2N HCl / 1.) 140 deg C, 14-18 h.; 2.) THF, 30 min.

2: 66 percent / p-TSA / benzene / Heating

3: 67 percent / thallium (III) nitrate trihydrate / tetrahydrofuran; methanol / 0.08 h / 0 °C

4: 92 percent / cuprous bromide-dimethyl sulphide complex / diethyl ether / -78 deg C, 2 h. then room temp.

5: 1.) borane-dimethyl sulphide; 2.) 3N NaOH, H₂O₂ / 1.) THF, 1 h.; 2.) THF, water

6: 71 percent / Et₃N, py*SO₃ / dimethylsulfoxide; CH₂Cl₂ / 0.58 h

7: 80 percent / CSA / benzene / 1 h / Heating

8: 52 percent / cuprous bromide-dimethyl sulphide complex / tetrahydrofuran; diethyl ether / 1 h / -50 °C

9: imidazole / dimethylformamide

10: 68 percent / LiAlH₄ / tetrahydrofuran / 0.5 h

11: 95 percent / CuSO₄ / 6 h

12: 69 percent / Tl(OCOCF₃)3, Na₂HPO₄ / tetrahydrofuran / 1 h / Ambient temperature

14: 96 percent / LiBH(Et)3 / tetrahydrofuran / 8 h

15: 1.) ozone; 2.) NaBH₄ / 1.) EtOH

16: 75 percent / n-Bu₃P / tetrahydrofuran / 8 h / Ambient temperature

17: 1.) ozone; 2.) Et₂NH / 1.) CH₂Cl₂, -78 deg C; 2.) CCl₄, reflux, 20 min.

18: 1.) n-BuLi, HMPA; 2.) TBAF / 1.) THF, hexane, -78 deg C then room temp.; 2.) THF, room temp., 1 h.

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; tributylphosphine; dimethylsulfide borane complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sulfur trioxide pyridine complex; lithium triethylborohydride; ozone; copper(II) sulfate; diethylamine; triethylamine; hydroquinone; thallium(III) nitrate; thallium(III) trifluoroacetate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)88114-X

Reference yield:

4β-formyl-4α,5α-dimethylcyclohex-2-enone (80267-24-9,87927-54-6) → (6α,18-dihydroxy)acetonide-12-phenylsulphonylcleroda-4,13(14)-dieno-16,15-lactone (87927-67-1,111819-85-3,111820-77-0)

Guidance literature:

Multi-step reaction with 17 steps

1: 66 percent / p-TSA / benzene / Heating

2: 67 percent / thallium (III) nitrate trihydrate / tetrahydrofuran; methanol / 0.08 h / 0 °C

3: 92 percent / cuprous bromide-dimethyl sulphide complex / diethyl ether / -78 deg C, 2 h. then room temp.

4: 1.) borane-dimethyl sulphide; 2.) 3N NaOH, H₂O₂ / 1.) THF, 1 h.; 2.) THF, water

5: 71 percent / Et₃N, py*SO₃ / dimethylsulfoxide; CH₂Cl₂ / 0.58 h

6: 80 percent / CSA / benzene / 1 h / Heating

7: 52 percent / cuprous bromide-dimethyl sulphide complex / tetrahydrofuran; diethyl ether / 1 h / -50 °C

8: imidazole / dimethylformamide

9: 68 percent / LiAlH₄ / tetrahydrofuran / 0.5 h

10: 95 percent / CuSO₄ / 6 h

11: 69 percent / Tl(OCOCF₃)3, Na₂HPO₄ / tetrahydrofuran / 1 h / Ambient temperature

13: 96 percent / LiBH(Et)3 / tetrahydrofuran / 8 h

14: 1.) ozone; 2.) NaBH₄ / 1.) EtOH

15: 75 percent / n-Bu₃P / tetrahydrofuran / 8 h / Ambient temperature

16: 1.) ozone; 2.) Et₂NH / 1.) CH₂Cl₂, -78 deg C; 2.) CCl₄, reflux, 20 min.

17: 1.) n-BuLi, HMPA; 2.) TBAF / 1.) THF, hexane, -78 deg C then room temp.; 2.) THF, room temp., 1 h.

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; tributylphosphine; dimethylsulfide borane complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sulfur trioxide pyridine complex; lithium triethylborohydride; ozone; copper(II) sulfate; diethylamine; triethylamine; thallium(III) nitrate; thallium(III) trifluoroacetate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)88114-X

Reference yield:

(1R,6S)-2-Methoxy-1,6-dimethyl-4-oxo-cyclohexanecarbaldehyde (111724-12-0,111819-86-4) → (6α,18-dihydroxy)acetonide-12-phenylsulphonylcleroda-4,13(14)-dieno-16,15-lactone (87927-67-1,111819-85-3,111820-77-0)

Guidance literature:

Multi-step reaction with 18 steps

1: 66 percent / p-TSA / benzene / 0.75 h / Heating

2: 66 percent / p-TSA / benzene / Heating

3: 67 percent / thallium (III) nitrate trihydrate / tetrahydrofuran; methanol / 0.08 h / 0 °C

4: 92 percent / cuprous bromide-dimethyl sulphide complex / diethyl ether / -78 deg C, 2 h. then room temp.

5: 1.) borane-dimethyl sulphide; 2.) 3N NaOH, H₂O₂ / 1.) THF, 1 h.; 2.) THF, water

6: 71 percent / Et₃N, py*SO₃ / dimethylsulfoxide; CH₂Cl₂ / 0.58 h

7: 80 percent / CSA / benzene / 1 h / Heating

8: 52 percent / cuprous bromide-dimethyl sulphide complex / tetrahydrofuran; diethyl ether / 1 h / -50 °C

9: imidazole / dimethylformamide

10: 68 percent / LiAlH₄ / tetrahydrofuran / 0.5 h

11: 95 percent / CuSO₄ / 6 h

12: 69 percent / Tl(OCOCF₃)3, Na₂HPO₄ / tetrahydrofuran / 1 h / Ambient temperature

14: 96 percent / LiBH(Et)3 / tetrahydrofuran / 8 h

15: 1.) ozone; 2.) NaBH₄ / 1.) EtOH

16: 75 percent / n-Bu₃P / tetrahydrofuran / 8 h / Ambient temperature

17: 1.) ozone; 2.) Et₂NH / 1.) CH₂Cl₂, -78 deg C; 2.) CCl₄, reflux, 20 min.

18: 1.) n-BuLi, HMPA; 2.) TBAF / 1.) THF, hexane, -78 deg C then room temp.; 2.) THF, room temp., 1 h.

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; copper(I) bromide dimethylsulfide complex; tributylphosphine; dimethylsulfide borane complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sulfur trioxide pyridine complex; lithium triethylborohydride; toluene-4-sulfonic acid; ozone; copper(II) sulfate; diethylamine; triethylamine; thallium(III) nitrate; thallium(III) trifluoroacetate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)88114-X

upstream raw materials:

ethyl 4-((tert-butyldimethylsilyl)oxy)but-2-ynoate

4α,5α-dimethyl-<(2α-hydroxy-1α-hydroxymethyl)-acetonide>-10-methylene-5β-(2''-phenylsulphonyl)ethyl-6β-bicyclo<4.4.0>decane

2-methylbut-2-enal

4β-formyl-4α,5α-dimethylcyclohex-2-enone

Downstream raw materials:

6α,18-dihydroxycleroda-4,13(14)-dieno-16,15-lactone

ajugarin I

4-epi-ajugarin I