(20S,22R,25ξ)-3β-<(tert-butyldiphenylsilyl)oxy>witha-5,23-dienolide

Base Information

Chemical Name:(20S,22R,25ξ)-3β-<(tert-butyldiphenylsilyl)oxy>witha-5,23-dienolide
CAS No.:140464-03-5
Molecular Formula:C₄₄H₆₀O₃Si
Molecular Weight:665.044
Hs Code.:

Synonyms:(20S,22R,25ξ)-3β-<(tert-butyldiphenylsilyl)oxy>witha-5,23-dienolide

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Chemical Property of (20S,22R,25ξ)-3β-<(tert-butyldiphenylsilyl)oxy>witha-5,23-dienolide

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Technology Process of (20S,22R,25ξ)-3β-<(tert-butyldiphenylsilyl)oxy>witha-5,23-dienolide

There total 8 articles about (20S,22R,25ξ)-3β-<(tert-butyldiphenylsilyl)oxy>witha-5,23-dienolide 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: 80.0%

: 140464-02-4
(20S,22S,23S)-23-acetoxy-3β-<(tert-butyldiphenylsilyl)oxy>witha-5,24-dienolide

: 140464-03-5
(20S,22R,25ξ)-3β-<(tert-butyldiphenylsilyl)oxy>witha-5,23-dienolide

Guidance literature:: With hydrogenchloride; amalgamated zinc; In diethyl ether; at -15 ℃;
DOI:10.1021/jo00036a032

Reference yield:

: 25819-77-6,56298-02-3,64681-78-3,64783-80-8,75658-37-6,104759-20-8
(S)-2-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-propionaldehyde

: 140464-03-5
(20S,22R,25ξ)-3β-<(tert-butyldiphenylsilyl)oxy>witha-5,23-dienolide

Guidance literature:: Multi-step reaction with 8 steps

1: 18.8 percent / tetrahydrofuran; hexane / -78 deg C to r.t.

2: 84.4 percent / anhydrous sodium acetate, N-bromosuccinimide / tetrahydrofuran; H₂O / 0.5 h / 0 °C

3: pyridinium chlorochromate, sodium acetate, celite / CH₂Cl₂ / 2 h / Ambient temperature

4: NaBH₄ / methanol / 0.5 h / 0 °C

5: 95.4 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 0 °C

6: 99.8 percent / p-toluenesulfonic acid, water / dioxane / 1 h / 80 °C

7: 99.2 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 6 h / Heating

8: 80 percent / zinc amalgam, HCl / diethyl ether / -15 °C

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; amalgamated zinc; N-Bromosuccinimide; Celite; water; sodium acetate; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; water;
DOI:10.1021/jo00036a032

Reference yield:

: 140463-97-4
(S)-6-[(S)-1-((3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-3,4-dimethyl-pyran-2,5-dione

: 140464-03-5
(20S,22R,25ξ)-3β-<(tert-butyldiphenylsilyl)oxy>witha-5,23-dienolide

Guidance literature:: Multi-step reaction with 5 steps

1: NaBH₄ / methanol / 0.5 h / 0 °C

2: 95.4 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 0 °C

3: 99.8 percent / p-toluenesulfonic acid, water / dioxane / 1 h / 80 °C

4: 99.2 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 6 h / Heating

5: 80 percent / zinc amalgam, HCl / diethyl ether / -15 °C

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; amalgamated zinc; water; toluene-4-sulfonic acid; triethylamine; In 1,4-dioxane; methanol; diethyl ether; dichloromethane;
DOI:10.1021/jo00036a032