3β-tosylpregna-5-en-(20R)-20,22-ethyl diether

Base Information

Chemical Name:3β-tosylpregna-5-en-(20R)-20,22-ethyl diether
CAS No.:188955-72-8
Molecular Formula:C₃₃H₅₀O₅S
Molecular Weight:558.823
Hs Code.:

Synonyms:3β-tosylpregna-5-en-(20R)-20,22-ethyl diether

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Chemical Property of 3β-tosylpregna-5-en-(20R)-20,22-ethyl diether

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Technology Process of 3β-tosylpregna-5-en-(20R)-20,22-ethyl diether

There total 12 articles about 3β-tosylpregna-5-en-(20R)-20,22-ethyl diether 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: 92.0%

: 98-59-9
p-toluenesulfonyl chloride

: 188955-71-7
3β-hydroxypregna-5-en-(20R)-20,22-ethyl diether

: 188955-72-8
3β-tosylpregna-5-en-(20R)-20,22-ethyl diether

Guidance literature:: With pyridine; at 30 ℃; for 12h;
DOI:10.1016/S0040-4020(97)00186-5

Reference yield:

: 979-02-2
16-dehydropregnenolone acetate

: 188955-72-8
3β-tosylpregna-5-en-(20R)-20,22-ethyl diether

Guidance literature:: Multi-step reaction with 12 steps

1.1: 97 percent / H₂ / Pd/C / 15 h / 30 °C / 2327.17 Torr

2.1: 96 percent / KOH / 2-methyl-propan-2-ol; H₂O / 16 h / 30 °C

3.1: 92 percent / imidazole / dimethylformamide / 8 h / 30 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -30 °C

4.2: 81 percent / tetrahydrofuran; hexane / 24 h / -30 - 0 °C

5.1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 30 °C

6.1: 81 percent / HgO; HgCl₂ / acetonitrile; H₂O / 7 h / Heating

7.1: 99 percent / pyridine / 12 h / 30 °C

8.1: 75 percent / KOAc / 4 h / Heating

9.1: 94 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 0 - 25 °C

10.1: NaH / dimethylformamide / 2 h / 25 - 60 °C

10.2: 72 percent / dimethylformamide / 5 h / 25 °C

11.1: 98 percent / PTSA / dioxane; H₂O / 2 h / 60 - 65 °C

12.1: 92 percent / pyridine / 12 h / 30 °C

With pyridine; 1H-imidazole; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; potassium acetate; sodium hydride; toluene-4-sulfonic acid; mercury dichloride; mercury(II) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; hexane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Hydrogenation / 2.1: Hydrolysis / 3.1: silylation / 4.1: Metallation / 4.2: Addition / 5.1: desilylation / 6.1: dedithioacetalation / 7.1: Tosylation / 8.1: methanolysis / 9.1: Reduction / 10.1: Metallation / 10.2: Etherification / 11.1: Ring cleavage / 12.1: Tosylation;
DOI:10.1016/S0040-4020(97)00186-5

Reference yield:

: 1778-02-5
Pregnenolone acetate

: 188955-72-8
3β-tosylpregna-5-en-(20R)-20,22-ethyl diether

Guidance literature:: Multi-step reaction with 11 steps

1.1: 96 percent / KOH / 2-methyl-propan-2-ol; H₂O / 16 h / 30 °C

2.1: 92 percent / imidazole / dimethylformamide / 8 h / 30 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -30 °C

3.2: 81 percent / tetrahydrofuran; hexane / 24 h / -30 - 0 °C

4.1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 30 °C

5.1: 81 percent / HgO; HgCl₂ / acetonitrile; H₂O / 7 h / Heating

6.1: 99 percent / pyridine / 12 h / 30 °C

7.1: 75 percent / KOAc / 4 h / Heating

8.1: 94 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / 0 - 25 °C

9.1: NaH / dimethylformamide / 2 h / 25 - 60 °C

9.2: 72 percent / dimethylformamide / 5 h / 25 °C

10.1: 98 percent / PTSA / dioxane; H₂O / 2 h / 60 - 65 °C

11.1: 92 percent / pyridine / 12 h / 30 °C

With pyridine; 1H-imidazole; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; potassium acetate; sodium hydride; toluene-4-sulfonic acid; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; 1,4-dioxane; hexane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Hydrolysis / 2.1: silylation / 3.1: Metallation / 3.2: Addition / 4.1: desilylation / 5.1: dedithioacetalation / 6.1: Tosylation / 7.1: methanolysis / 8.1: Reduction / 9.1: Metallation / 9.2: Etherification / 10.1: Ring cleavage / 11.1: Tosylation;
DOI:10.1016/S0040-4020(97)00186-5