(3α,4α,4aβ,5β,6α)-4-acetamido-5,6-(cyclohexylidenedioxy)-3,4,4a,5,6,7-hexahydro-8-hydroxy-3-methylisocoumarin

Base Information

• Chemical Name: (3α,4α,4aβ,5β,6α)-4-acetamido-5,6-(cyclohexylidenedioxy)-3,4,4a,5,6,7-hexahydro-8-hydroxy-3-methylisocoumarin
• CAS No.: 98903-69-6
• Molecular Formula: C₁₈H₂₅NO₆
• Molecular Weight: 351.4
• Mol file: 98903-69-6.mol

Synonyms:

Chemical Property of (3α,4α,4aβ,5β,6α)-4-acetamido-5,6-(cyclohexylidenedioxy)-3,4,4a,5,6,7-hexahydro-8-hydroxy-3-methylisocoumarin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3α,4α,4aβ,5β,6α)-4-acetamido-5,6-(cyclohexylidenedioxy)-3,4,4a,5,6,7-hexahydro-8-hydroxy-3-methylisocoumarin

There total 26 articles about (3α,4α,4aβ,5β,6α)-4-acetamido-5,6-(cyclohexylidenedioxy)-3,4,4a,5,6,7-hexahydro-8-hydroxy-3-methylisocoumarin 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: 72.0%

<1β,2α(1R*,2R*),3β,4α,6β>-2-<1-acetamido-2-hydroxypropyl>-3,4-(cyclohexylidenedioxy)-6-hydroxycyclohexanecarboxylic acid, δ-lactone (98903-68-5) → (3α,4α,4aβ,5β,6α)-4-acetamido-5,6-(cyclohexylidenedioxy)-3,4,4a,5,6,7-hexahydro-8-hydroxy-3-methylisocoumarin (98903-69-6,106499-53-0)

Guidance literature:

With pyridine; chromium(VI) oxide; In dichloromethane; for 1.25h;

DOI:10.1021/jo00380a025

Reference yield: 52.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → C18H25NO6 (98903-69-6,106499-53-0)

Guidance literature:

With toluene-4-sulfonic acid; trimethyl orthoformate; In various solvent(s); for 6h; Heating;

DOI:10.1021/jo00380a025

Reference yield:

(1aα,3α,3aα,7aβ,7bα)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1a,2,3,3a,7a,7b-hexahydro-6-methyl-5H-oxireno<1>benzopyran-5-one (98903-51-6) → (3α,4α,4aβ,5β,6α)-4-acetamido-5,6-(cyclohexylidenedioxy)-3,4,4a,5,6,7-hexahydro-8-hydroxy-3-methylisocoumarin (98903-69-6,106499-53-0)

Guidance literature:

Multi-step reaction with 22 steps

1: 86 percent / diisobutylaluminum hydride / toluene; hexane / 2.5 h / -78 - -40 °C

2: 85 percent / BF₃*OEt₂ / 6 h / -20 °C

3: boron trifluoride etherate / hexane; tetrahydrofuran / 3 h / -78 °C

4: 1.) NaH, tetra-n-butylammonium iodide / 1.) THF, 2.) RT, 21 h

5: 90 percent / H₂, quinoline / Lindlar's cat. / CH₂Cl₂; methanol / 6 h

6: 0.5 N aq. HCl / dioxane / 10 h / Ambient temperature

7: pyridine, dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

8: 0.25 N aq. HCl / dioxane / 1 h / Ambient temperature

9: 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 2 h / -40 °C

10: 1.) tetra-N-butylammonium azide, 2.) OsO₄, N-methylmorpholine N-oxide / 1.) CH₂Cl₂, -40 deg C, 35 min, 2.) THF, RT, 20 h

11: pyridinium p-toluenesulfonate / CH₂Cl₂ / 5.5 h

12: 1.) ozone, 2.) dimethyl sulfide / 1.) CH₂Cl₂, MeOH, NaHCO₃, -78 deg C, 2 min, 2.) RT, 4 h

13: NaIO₄, RuO₂ / CCl₄; acetonitrile; H₂O / 5.5 h / 0 °C

14: diethyl ether / 0.5 h / 0 °C

15: 0.25 N aq. HCl / dioxane / 12 h

16: NaIO₄ / methanol; H₂O / 38 h / Ambient temperature

17: NaBH₄ / methanol / 4 h / Ambient temperature

18: 93 percent / p-TsOH*H₂O / benzene / 1 h / Heating

19: 16.3 mg / trimethyl orthoformate, p-TsOH / benzene / 12 h / Ambient temperature

20: 81 percent / Lindlar's cat. / ethyl acetate / 7.5 h

21: 98 percent / H₂ / Pd(OH)2 / ethanol / 3 h

22: 72 percent / pyridine, CrO₃ / CH₂Cl₂ / 1.25 h

With pyridine; quinoline; chromium(VI) oxide; hydrogenchloride; dmap; ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; Lindlar's catalyst; osmium(VIII) oxide; dimethylsulfide; boron trifluoride diethyl etherate; hydrogen; tetrabutylammoniun azide; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triethylamine; trimethyl orthoformate; palladium dihydroxide; Lindlar's catalyst; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; diethyl ether; ethanol; hexane; dichloromethane; water; ethyl acetate; toluene; acetonitrile; benzene;

DOI:10.1021/jo00380a025

upstream raw materials:

cyclohexanone

acetic anhydride

Desalanylactionobolin hydrochloride

<1β,2α(1R*,2R*),3β,4α,6β>-2-<1-acetamido-2-hydroxypropyl>-3,4-(cyclohexylidenedioxy)-6-hydroxycyclohexanecarboxylic acid, δ-lactone