(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

Base Information

• Chemical Name: (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
• CAS No.: 140181-52-8
• Molecular Formula: C₃₇H₆₁NO₈Si
• Molecular Weight: 675.979
• Mol file: 140181-52-8.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 21 articles about (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 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: 91.0%

(1α,2β,3β,4β,4aα,8α,8aβ)-(+/-)-decahydro-1-<3-<5-methyl-5-<<(1,1-dimethylethyl)dimethylsilyl>ethoxy>>-4,5-dihydroisoxazolyl>-8-(4-methoxybenzyloxy)-2,5,5,8a-tetramethyl-1,2,3,4-naphthalenetetraol (140181-51-7,140181-56-2) + 2,2-dimethoxy-propane (77-76-9) → (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 (140181-52-8,140385-04-2)

Guidance literature:

With pyridinium p-toluenesulfonate; for 24h; Ambient temperature;

Reference yield:

(1α,4aβ,8aβ)-(+/-)-1,2,3,4-tetrahydro-1-hydroxy-4,4,7,8a-tetramethyl-(4aH,8aH)-naphthalene-5,8-dione (123218-01-9,130815-12-2) → (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 (140181-52-8,140385-04-2)

Guidance literature:

Multi-step reaction with 16 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

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; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc dibromide; Pd-BaSO₄; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; chloroform; water; ethylene glycol; toluene;

Reference yield:

(6α,6aβ,9aβ,9bβ)-(+/-)-6-hydroxy-5,6,6a,7,8,9,9a,9b-octahydro-4,7,7,9b-tetramethyl-naphtho<1.8-de>-1,3-dioxin (140181-32-4) → (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 (140181-52-8,140385-04-2)

Guidance literature:

Multi-step reaction with 18 steps

1: 82 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 0.5 h / Ambient temperature

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

3: 80 percent / P₂O₅ / CHCl₃ / 2 h / 0 °C

4: 93 percent

5: 87 percent / H₂, quinoline / 10percent Pd/BaSO₄ / methanol / 2 h / 1551.4 Torr / Ambient temperature

6: 80 percent / sodium, methanol / 48 h / Heating

7: ozone, pyridine / CH₂Cl₂ / -78 °C

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

9: DIBAH, pyridine / toluene / -78 °C

10: 96.7 percent / pyridine / 24 h / Ambient temperature

11: 100 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 90 °C

12: 89 percent / zinc bromide / CH₂Cl₂ / 7 h / Ambient temperature

13: NaH / hexamethylphosphoric acid triamide; tetrahydrofuran

14: 100 percent / potassium carbonate / H₂O / 2 h / Ambient temperature

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

16: Et₃N / CHCl₃ / 0.33 h / Heating

17: 65 percent / potassium hydroxide / ethane-1,2-diol / 24 h / 80 °C

18: 91 percent / pyridinium p-toluenesulfonate / 24 h / Ambient temperature

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

upstream raw materials:

(1α,2β,3β,4β,4aα,8α,8aβ)-(+/-)-decahydro-1-<3-<5-methyl-5-<<(1,1-dimethylethyl)dimethylsilyl>ethoxy>>-4,5-dihydroisoxazolyl>-8-(4-methoxybenzyloxy)-2,5,5,8a-tetramethyl-1,2,3,4-naphthalenetetraol

2,2-dimethoxy-propane

(1α,4aβ,8aβ)-(+/-)-1,2,3,4-tetrahydro-1-hydroxy-4,4,7,8a-tetramethyl-(4aH,8aH)-naphthalene-5,8-dione

(6α,6aβ,9aβ,9bβ)-(+/-)-6-hydroxy-5,6,6a,7,8,9,9a,9b-octahydro-4,7,7,9b-tetramethyl-naphtho<1.8-de>-1,3-dioxin

Downstream raw materials:

<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