1α,2β,3β-Triacetoxy-4α-methyl-13-oxo-8β-(phenylselenocarbonyl)methyl-17,18-dinor-16,17-seco-5α,14β-androstan-16,7α-lacton

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Chemical Name:1α,2β,3β-Triacetoxy-4α-methyl-13-oxo-8β-(phenylselenocarbonyl)methyl-17,18-dinor-16,17-seco-5α,14β-androstan-16,7α-lacton
CAS No.:76389-74-7
Molecular Formula:C₃₂H₃₈O₁₀Se
Molecular Weight:661.608
Hs Code.:

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Chemical Property of 1α,2β,3β-Triacetoxy-4α-methyl-13-oxo-8β-(phenylselenocarbonyl)methyl-17,18-dinor-16,17-seco-5α,14β-androstan-16,7α-lacton

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Technology Process of 1α,2β,3β-Triacetoxy-4α-methyl-13-oxo-8β-(phenylselenocarbonyl)methyl-17,18-dinor-16,17-seco-5α,14β-androstan-16,7α-lacton

There total 26 articles about 1α,2β,3β-Triacetoxy-4α-methyl-13-oxo-8β-(phenylselenocarbonyl)methyl-17,18-dinor-16,17-seco-5α,14β-androstan-16,7α-lacton 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:

: Acetic acid (1S,4R,5S,8S,9S,10S,13S,14S,17S)-17-hydroxy-4,10,13-trimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-1-yl ester

: 76389-74-7
1α,2β,3β-Triacetoxy-4α-methyl-13-oxo-8β-(phenylselenocarbonyl)methyl-17,18-dinor-16,17-seco-5α,14β-androstan-16,7α-lacton

Guidance literature:: Multi-step reaction with 23 steps

1: Jones-reagent / acetone / 0.02 h / 0 °C

2: 80 percent / N-Methylmorpholine N-oxide, osmium tetroxide / tetrahydrofuran / 144 h

3: 98 percent / p-toluenesulfonic acid / 2 h / Ambient temperature

4: 1.) 0.8 M potassium tert-butoxide, 2.) pentyl nitrite / toluene; 2-methyl-propan-2-ol / 2 h / Ambient temperature

5: p-toluenesulfonic acid / CH₂Cl₂ / 3 h / Ambient temperature

6: potassium hydroxide / dioxane; H₂O / 15 h / Ambient temperature

7: p-toluenesulfonic acid / dioxane; H₂O / 2 h / 70 °C

8: pyridine / 1.5 h / 70 °C

9: 13 percent / Copper(II)acetate / acetic acid; pyridine; dimethylsulfoxide / 1.5 h / Ambient temperature

10: 80 percent / O₃ / CH₂Cl₂; pyridine / -78 °C

11: cc. HCl solution / methanol / 3 h / Heating

12: 0.33 h / Ambient temperature

13: pyridine / 16 h / Ambient temperature

14: 29 percent / pyrrolidone, pyrrolidone hydrotribromide / tetrahydrofuran / 0.67 h / 50 °C

15: 86 percent / lithium bromide, lithium carbonate / dimethylformamide / 0.33 h / 120 °C

16: 57 percent / p-toluenesulfonic acid / 1.5 h / 80 °C

17: 65 percent / m-chloroperbenzoic acid, 4 N NaOH / H₂O; dioxane / 3 h / Ambient temperature

18: tetrahydrofuran / -78 °C / Irradiation

19: p-toluenesulfonic acid / dioxane / 2 h / Ambient temperature; Irradiation

20: O₃ / methanol / 0.13 h / -78 °C

21: triethylamine / 6 h / Ambient temperature

22: oxalyl chloride / benzene / 0.75 h / Ambient temperature

23: pyridine / benzene; tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; 2-pyrrolidinon; hydrogenchloride; potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; oxalyl dichloride; pyrrolidone hydrotribromide; n-Amyl nitrite; Jones-reagent; potassium tert-butylate; copper diacetate; lithium carbonate; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene;
DOI:10.1002/hlca.19800630625

Reference yield:

: ((1S,4aS,4bR,5R,6R,7R,8S,8aS,10aR)-5,6,7-Trihydroxy-4b,8-dimethyl-2-oxo-tetradecahydro-phenanthren-1-yl)-acetic acid methyl ester

: 76389-74-7
1α,2β,3β-Triacetoxy-4α-methyl-13-oxo-8β-(phenylselenocarbonyl)methyl-17,18-dinor-16,17-seco-5α,14β-androstan-16,7α-lacton

Guidance literature:: Multi-step reaction with 11 steps

1: pyridine / 16 h / Ambient temperature

2: 29 percent / pyrrolidone, pyrrolidone hydrotribromide / tetrahydrofuran / 0.67 h / 50 °C

3: 86 percent / lithium bromide, lithium carbonate / dimethylformamide / 0.33 h / 120 °C

4: 57 percent / p-toluenesulfonic acid / 1.5 h / 80 °C

5: 65 percent / m-chloroperbenzoic acid, 4 N NaOH / H₂O; dioxane / 3 h / Ambient temperature

6: tetrahydrofuran / -78 °C / Irradiation

7: p-toluenesulfonic acid / dioxane / 2 h / Ambient temperature; Irradiation

8: O₃ / methanol / 0.13 h / -78 °C

9: triethylamine / 6 h / Ambient temperature

10: oxalyl chloride / benzene / 0.75 h / Ambient temperature

11: pyridine / benzene; tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; 2-pyrrolidinon; sodium hydroxide; oxalyl dichloride; pyrrolidone hydrotribromide; lithium carbonate; toluene-4-sulfonic acid; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; benzene;
DOI:10.1002/hlca.19800630625

Reference yield:

: (1S,4R,5S,8S,9S,10S,13S,14S,17S)-4,10,13-Trimethyl-17-(tetrahydro-pyran-2-yloxy)-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-1-ol

: 76389-74-7
1α,2β,3β-Triacetoxy-4α-methyl-13-oxo-8β-(phenylselenocarbonyl)methyl-17,18-dinor-16,17-seco-5α,14β-androstan-16,7α-lacton

Guidance literature:: Multi-step reaction with 25 steps

1: pyridine

2: H₃O⁽¹⁺⁾

3: Jones-reagent / acetone / 0.02 h / 0 °C

4: 80 percent / N-Methylmorpholine N-oxide, osmium tetroxide / tetrahydrofuran / 144 h

5: 98 percent / p-toluenesulfonic acid / 2 h / Ambient temperature

6: 1.) 0.8 M potassium tert-butoxide, 2.) pentyl nitrite / toluene; 2-methyl-propan-2-ol / 2 h / Ambient temperature

7: p-toluenesulfonic acid / CH₂Cl₂ / 3 h / Ambient temperature

8: potassium hydroxide / dioxane; H₂O / 15 h / Ambient temperature

9: p-toluenesulfonic acid / dioxane; H₂O / 2 h / 70 °C

10: pyridine / 1.5 h / 70 °C

11: 13 percent / Copper(II)acetate / acetic acid; pyridine; dimethylsulfoxide / 1.5 h / Ambient temperature

12: 80 percent / O₃ / CH₂Cl₂; pyridine / -78 °C

13: cc. HCl solution / methanol / 3 h / Heating

14: 0.33 h / Ambient temperature

15: pyridine / 16 h / Ambient temperature

16: 29 percent / pyrrolidone, pyrrolidone hydrotribromide / tetrahydrofuran / 0.67 h / 50 °C

17: 86 percent / lithium bromide, lithium carbonate / dimethylformamide / 0.33 h / 120 °C

18: 57 percent / p-toluenesulfonic acid / 1.5 h / 80 °C

19: 65 percent / m-chloroperbenzoic acid, 4 N NaOH / H₂O; dioxane / 3 h / Ambient temperature

20: tetrahydrofuran / -78 °C / Irradiation

21: p-toluenesulfonic acid / dioxane / 2 h / Ambient temperature; Irradiation

22: O₃ / methanol / 0.13 h / -78 °C

23: triethylamine / 6 h / Ambient temperature

24: oxalyl chloride / benzene / 0.75 h / Ambient temperature

25: pyridine / benzene; tetrahydrofuran / 0.5 h / Ambient temperature

With pyridine; 2-pyrrolidinon; hydrogenchloride; potassium hydroxide; sodium hydroxide; osmium(VIII) oxide; oxalyl dichloride; pyrrolidone hydrotribromide; n-Amyl nitrite; Jones-reagent; oxonium; potassium tert-butylate; copper diacetate; lithium carbonate; toluene-4-sulfonic acid; ozone; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene;
DOI:10.1002/hlca.19800630625