(1aα,3α,3aα,7aβ,7bα)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>octahydro-6-methyl-6-(phenylseleno)-5H-oxireno<1>benzopyran-5-one

Base Information

• Chemical Name: (1aα,3α,3aα,7aβ,7bα)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>octahydro-6-methyl-6-(phenylseleno)-5H-oxireno<1>benzopyran-5-one
• CAS No.: 98974-83-5
• Molecular Formula: C₂₂H₃₂O₄SeSi
• Molecular Weight: 467.539
• Mol file: 98974-83-5.mol

Synonyms:

Chemical Property of (1aα,3α,3aα,7aβ,7bα)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>octahydro-6-methyl-6-(phenylseleno)-5H-oxireno<1>benzopyran-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1aα,3α,3aα,7aβ,7bα)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>octahydro-6-methyl-6-(phenylseleno)-5H-oxireno<1>benzopyran-5-one

There total 1 articles about (1aα,3α,3aα,7aβ,7bα)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>octahydro-6-methyl-6-(phenylseleno)-5H-oxireno<1>benzopyran-5-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:

Phenylselenyl chloride (5707-04-0) + (1aR,3R,3aR,7aS,7bS)-3-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-octahydro-1,4-dioxa-cyclopropa[a]naphthalen-5-one (98903-49-2,98974-82-4,106499-49-4) → (1aα,3α,3aα,7aβ,7bα)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>octahydro-6-methyl-6-(phenylseleno)-5H-oxireno<1>benzopyran-5-one (98903-50-5,98974-83-5)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, -78 deg C, 1 h;

DOI:10.1021/jo00380a025

Reference yield:

(1aα,3α,3aα,7aβ,7bα)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>octahydro-6-methyl-6-(phenylseleno)-5H-oxireno<1>benzopyran-5-one (98903-50-5,98974-83-5) → methyl <1α,2α(1R*),3β,4α,6β>-2-(1-azido-2-hydroxypropyl)-3,4-dihydroxy-6-(phenylmethoxy)cyclohexanecarboxylate

Guidance literature:

Multi-step reaction with 18 steps

1: 92 percent / mCPBA / CCl₄; CH₂Cl₂ / 3.5 h / -22 °C

2: 86 percent / diisobutylaluminum hydride / toluene; hexane / 2.5 h / -78 - -40 °C

3: 85 percent / BF₃*OEt₂ / 6 h / -20 °C

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

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

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

7: 0.5 N aq. HCl / dioxane / 10 h / Ambient temperature

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

9: 0.25 N aq. HCl / dioxane / 1 h / Ambient temperature

10: 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 2 h / -40 °C

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

12: pyridinium p-toluenesulfonate / CH₂Cl₂ / 5.5 h

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

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

15: diethyl ether / 0.5 h / 0 °C

16: 0.25 N aq. HCl / dioxane / 12 h

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

18: NaBH₄ / methanol / 4 h / Ambient temperature

With pyridine; quinoline; hydrogenchloride; dmap; ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; dimethylsulfide; boron trifluoride diethyl etherate; hydrogen; tetrabutylammoniun azide; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; ozone; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo00380a025

Reference yield:

(1aα,3α,3aα,7aβ,7bα)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>octahydro-6-methyl-6-(phenylseleno)-5H-oxireno<1>benzopyran-5-one (98903-50-5,98974-83-5) → Acetic acid (2R,4aR,5S,6S,8S,8aS)-6-benzyloxy-2-methanesulfonyloxy-5-((Z)-3-methoxy-propenyl)-3-methyl-4a,5,6,7,8,8a-hexahydro-2H-chromen-8-yl ester

Guidance literature:

Multi-step reaction with 10 steps

1: 92 percent / mCPBA / CCl₄; CH₂Cl₂ / 3.5 h / -22 °C

2: 86 percent / diisobutylaluminum hydride / toluene; hexane / 2.5 h / -78 - -40 °C

3: 85 percent / BF₃*OEt₂ / 6 h / -20 °C

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

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

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

7: 0.5 N aq. HCl / dioxane / 10 h / Ambient temperature

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

9: 0.25 N aq. HCl / dioxane / 1 h / Ambient temperature

10: 4-(dimethylamino)pyridine, Et₃N / CH₂Cl₂ / 2 h / -40 °C

With pyridine; quinoline; hydrogenchloride; dmap; boron trifluoride diethyl etherate; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; hexane; dichloromethane; toluene;

DOI:10.1021/jo00380a025

upstream raw materials:

Phenylselenyl chloride

(1aR,3R,3aR,7aS,7bS)-3-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-octahydro-1,4-dioxa-cyclopropa[a]naphthalen-5-one

Downstream raw materials:

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

(2S,4aR,5S,6S,8S,8aS)-6-Benzyloxy-5-((Z)-3-methoxy-propenyl)-3-methyl-4a,5,6,7,8,8a-hexahydro-2H-chromene-2,8-diol

(4aβ,5α,6β,8α,8aα)-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propynyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol

<4aβ,5α(Z),6β,8α,8aα>-4a,5,6,7,8,8a-hexahydro-5-(3-methoxy-1-propenyl)-3-methyl-6-(phenylmethoxy)-2H-1-benzopyran-2,8-diol 8-acetate