(4aR,6S,7S,7aR)-6-{[tert-butyl(dimethyl)silyl]oxy}-7-methyl-4-methylene-2-[(4-methylphenyl)sulfonyl]octahydro-1H-cyclopenta[c]pyridine

Base Information

Chemical Name:(4aR,6S,7S,7aR)-6-{[tert-butyl(dimethyl)silyl]oxy}-7-methyl-4-methylene-2-[(4-methylphenyl)sulfonyl]octahydro-1H-cyclopenta[c]pyridine
CAS No.:823787-98-0
Molecular Formula:C₂₃H₃₇NO₃SSi
Molecular Weight:435.703
Hs Code.:

Synonyms:(4aR,6S,7S,7aR)-6-{[tert-butyl(dimethyl)silyl]oxy}-7-methyl-4-methylene-2-[(4-methylphenyl)sulfonyl]octahydro-1H-cyclopenta[c]pyridine

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Chemical Property of (4aR,6S,7S,7aR)-6-{[tert-butyl(dimethyl)silyl]oxy}-7-methyl-4-methylene-2-[(4-methylphenyl)sulfonyl]octahydro-1H-cyclopenta[c]pyridine

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Technology Process of (4aR,6S,7S,7aR)-6-{[tert-butyl(dimethyl)silyl]oxy}-7-methyl-4-methylene-2-[(4-methylphenyl)sulfonyl]octahydro-1H-cyclopenta[c]pyridine

There total 11 articles about (4aR,6S,7S,7aR)-6-{[tert-butyl(dimethyl)silyl]oxy}-7-methyl-4-methylene-2-[(4-methylphenyl)sulfonyl]octahydro-1H-cyclopenta[c]pyridine 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: 93.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 823787-97-9
(4aR,6S,7S,7aR)-7-methyl-4-methylene-2-[(4-methylphenyl)sulfonyl]octahydro-1H-cyclopenta[c]pyridin-6-ol

: 823787-98-0
(4aR,6S,7S,7aR)-6-{[tert-butyl(dimethyl)silyl]oxy}-7-methyl-4-methylene-2-[(4-methylphenyl)sulfonyl]octahydro-1H-cyclopenta[c]pyridine

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1021/ja0401702

Reference yield:

: 823788-10-9
(1S,2S,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-3-oxocyclopentanecarbaldehyde

: 823787-98-0
(4aR,6S,7S,7aR)-6-{[tert-butyl(dimethyl)silyl]oxy}-7-methyl-4-methylene-2-[(4-methylphenyl)sulfonyl]octahydro-1H-cyclopenta[c]pyridine

Guidance literature:: Multi-step reaction with 7 steps

1: 71 percent / sodium borohydride / tetrahydrofuran; ethanol / 0.5 h

2: 99 percent / triphenylphosphine; diethyl azidocarboxylate / tetrahydrofuran / 1 h / 20 °C

3: 95 percent / trifluoroacetic acid / CH₂Cl₂ / 16 h / 20 °C

4: 81 percent / K₂CO₃ / acetonitrile / 3 h / Heating

5: 10 percent / palladium(II) acetate; N,N'-bis(benzylidene)ethylenediamine; poly(methylhydrosiloxane) / acetic acid / benzene / 4 h / 95 °C

6: 97 percent / sodium borohydrate / methanol / 0.5 h

7: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; N,N'-bis(benzyliden)ethylendiamine; palladium diacetate; potassium carbonate; triphenylphosphine; trifluoroacetic acid; poly(methylhydrosiloxane); diethylazodicarboxylate; acetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene; 2: Mitsunobu reaction;
DOI:10.1021/ja0401702

Reference yield:

: 56745-67-6,61305-35-9,61740-33-8,61305-36-0
(4S)-4-tert-butyldimethylsilyloxycyclopent-2-en-1-one

: 823787-98-0
(4aR,6S,7S,7aR)-6-{[tert-butyl(dimethyl)silyl]oxy}-7-methyl-4-methylene-2-[(4-methylphenyl)sulfonyl]octahydro-1H-cyclopenta[c]pyridine

Guidance literature:: Multi-step reaction with 9 steps

1.1: butyllithium; dimethylzinc / tetrahydrofuran; hexane / 0.25 h / 0 °C

1.2: tetrahydrofuran; hexane / 0.25 h / -78 °C

1.3: 77 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 16 h / -40 °C

2.1: ozone / CH₂Cl₂; methanol / -78 °C

2.2: 96 percent / methyl sulfide / CH₂Cl₂; methanol / 2 h / 20 °C

3.1: 71 percent / sodium borohydride / tetrahydrofuran; ethanol / 0.5 h

4.1: 99 percent / triphenylphosphine; diethyl azidocarboxylate / tetrahydrofuran / 1 h / 20 °C

5.1: 95 percent / trifluoroacetic acid / CH₂Cl₂ / 16 h / 20 °C

6.1: 81 percent / K₂CO₃ / acetonitrile / 3 h / Heating

7.1: 10 percent / palladium(II) acetate; N,N'-bis(benzylidene)ethylenediamine; poly(methylhydrosiloxane) / acetic acid / benzene / 4 h / 95 °C

8.1: 97 percent / sodium borohydrate / methanol / 0.5 h

9.1: 93 percent / imidazole / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; N,N'-bis(benzyliden)ethylendiamine; dimethyl zinc(II); palladium diacetate; potassium carbonate; ozone; triphenylphosphine; trifluoroacetic acid; poly(methylhydrosiloxane); diethylazodicarboxylate; acetic acid; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene; 4.1: Mitsunobu reaction;
DOI:10.1021/ja0401702