<3aα,4α,5α,5(EZ),5aβ,6α,9aα,9bα>-(+/-)-1--2,2,4,5a,9,9-hexamethylnaphtho<1,2-d>-1,3-dioxol-5-yl>-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-2-penten-1-one

Base Information

Chemical Name:<3aα,4α,5α,5(EZ),5aβ,6α,9aα,9bα>-(+/-)-1--2,2,4,5a,9,9-hexamethylnaphtho<1,2-d>-1,3-dioxol-5-yl>-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-2-penten-1-one
CAS No.:140181-53-9
Molecular Formula:C₃₇H₆₀O₈Si
Molecular Weight:660.964
Hs Code.:

<3aα,4α,5α,5(EZ),5aβ,6α,9aα,9bα>-(+/-)-1-<decahydro-4,5-dihydroxy-6-<4-methoxybenzyloxy>-2,2,4,5a,9,9-hexamethylnaphtho<1,2-d>-1,3-dioxol-5-yl>-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-2-penten-1-one

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Chemical Property of <3aα,4α,5α,5(EZ),5aβ,6α,9aα,9bα>-(+/-)-1--2,2,4,5a,9,9-hexamethylnaphtho<1,2-d>-1,3-dioxol-5-yl>-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-2-penten-1-one

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Technology Process of <3aα,4α,5α,5(EZ),5aβ,6α,9aα,9bα>-(+/-)-1--2,2,4,5a,9,9-hexamethylnaphtho<1,2-d>-1,3-dioxol-5-yl>-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-2-penten-1-one

There total 22 articles about <3aα,4α,5α,5(EZ),5aβ,6α,9aα,9bα>-(+/-)-1--2,2,4,5a,9,9-hexamethylnaphtho<1,2-d>-1,3-dioxol-5-yl>-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-2-penten-1-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: 85.0%

: 140181-52-8,140385-04-2
(3aα,4α,5α,5aβ,6α,9aα,9bα)-(+/-)-decahydro-5-<3-<5-methyl-5-<<(1,1-dimethylethyl)dimethylsilyl>ethoxy>>-4,5-dihydroisoxazolyl>-4,5-dihydroxy-6-<4-methoxybenzyloxy>-2,2,4-5a,9,9-hexamethylnaphtho<1,2-d>-1,3-dioxol

: 140181-53-9,140385-05-3
<3aα,4α,5α,5(EZ),5aβ,6α,9aα,9bα>-(+/-)-1--2,2,4,5a,9,9-hexamethylnaphtho<1,2-d>-1,3-dioxol-5-yl>-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-2-penten-1-one

Guidance literature:: With hydrogen; acetic acid; W 2 Ni-Raney; In methanol; water; for 24h; Ambient temperature;

Reference yield:

: 123218-01-9,130815-12-2
(1α,4aβ,8aβ)-(+/-)-1,2,3,4-tetrahydro-1-hydroxy-4,4,7,8a-tetramethyl-(4aH,8aH)-naphthalene-5,8-dione

: 140181-53-9,140385-05-3
<3aα,4α,5α,5(EZ),5aβ,6α,9aα,9bα>-(+/-)-1--2,2,4,5a,9,9-hexamethylnaphtho<1,2-d>-1,3-dioxol-5-yl>-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-2-penten-1-one

Guidance literature:: Multi-step reaction with 17 steps

1: 80 percent / P₂O₅ / CHCl₃ / 2 h / 0 °C

2: 93 percent

3: 87 percent / H₂, quinoline / 10percent Pd/BaSO₄ / methanol / 2 h / 1551.4 Torr / Ambient temperature

4: 80 percent / sodium, methanol / 48 h / Heating

5: ozone, pyridine / CH₂Cl₂ / -78 °C

6: hydroxylamine hydrochloride, pyridine / ethanol / 0.75 h / Heating

7: DIBAH, pyridine / toluene / -78 °C

8: 96.7 percent / pyridine / 24 h / Ambient temperature

9: 100 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 90 °C

10: 89 percent / zinc bromide / CH₂Cl₂ / 7 h / Ambient temperature

11: NaH / hexamethylphosphoric acid triamide; tetrahydrofuran

12: 100 percent / potassium carbonate / H₂O / 2 h / Ambient temperature

13: N-chlorosuccinimide, pyridine / CHCl₃ / 0.17 h

14: Et₃N / CHCl₃ / 0.33 h / Heating

15: 65 percent / potassium hydroxide / ethane-1,2-diol / 24 h / 80 °C

16: 91 percent / pyridinium p-toluenesulfonate / 24 h / Ambient temperature

17: 85 percent / H₂, AcOH / W 2 Ni-Raney / methanol; H₂O / 24 h / Ambient temperature

With pyridine; quinoline; methanol; potassium hydroxide; N-chloro-succinimide; hydroxylamine hydrochloride; hydrogen; sodium; phosphorus pentoxide; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc dibromide; Pd-BaSO₄; W 2 Ni-Raney; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; chloroform; water; ethylene glycol; toluene;

Reference yield:

: 140181-33-5
(6aβ,9aβ,9bβ)-(+/-)-6a,7,8,9,9a,9b-hexahydro-4,7,7,9b-tetramethyl-(5H)-naphtho<1.8-de>-1,3-dioxin-6-one

: 140181-53-9,140385-05-3
<3aα,4α,5α,5(EZ),5aβ,6α,9aα,9bα>-(+/-)-1--2,2,4,5a,9,9-hexamethylnaphtho<1,2-d>-1,3-dioxol-5-yl>-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-2-penten-1-one

Guidance literature:: Multi-step reaction with 18 steps

1: 1.) m-chloroperbenzoic acid 2.) silica gel / 1.) methylene dichloride, room temp., 3 h 2.) reflux, 15 h

2: 80 percent / P₂O₅ / CHCl₃ / 2 h / 0 °C

3: 93 percent

4: 87 percent / H₂, quinoline / 10percent Pd/BaSO₄ / methanol / 2 h / 1551.4 Torr / Ambient temperature

5: 80 percent / sodium, methanol / 48 h / Heating

6: ozone, pyridine / CH₂Cl₂ / -78 °C

7: hydroxylamine hydrochloride, pyridine / ethanol / 0.75 h / Heating

8: DIBAH, pyridine / toluene / -78 °C

9: 96.7 percent / pyridine / 24 h / Ambient temperature

10: 100 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 90 °C

11: 89 percent / zinc bromide / CH₂Cl₂ / 7 h / Ambient temperature

12: NaH / hexamethylphosphoric acid triamide; tetrahydrofuran

13: 100 percent / potassium carbonate / H₂O / 2 h / Ambient temperature

14: N-chlorosuccinimide, pyridine / CHCl₃ / 0.17 h

15: Et₃N / CHCl₃ / 0.33 h / Heating

16: 65 percent / potassium hydroxide / ethane-1,2-diol / 24 h / 80 °C

17: 91 percent / pyridinium p-toluenesulfonate / 24 h / Ambient temperature

18: 85 percent / H₂, AcOH / W 2 Ni-Raney / methanol; H₂O / 24 h / Ambient temperature

With pyridine; quinoline; methanol; potassium hydroxide; N-chloro-succinimide; hydroxylamine hydrochloride; hydrogen; sodium; phosphorus pentoxide; pyridinium p-toluenesulfonate; silica gel; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc dibromide; Pd-BaSO₄; W 2 Ni-Raney; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; chloroform; water; ethylene glycol; toluene;