2-((1S,2S,5S,6S)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-oxocyclohexyl)ethyl pivalate

Base Information

Chemical Name:2-((1S,2S,5S,6S)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-oxocyclohexyl)ethyl pivalate
CAS No.:1417600-72-6
Molecular Formula:C₂₇H₄₇NO₄Si
Molecular Weight:477.76
Hs Code.:

Synonyms:2-((1S,2S,5S,6S)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-oxocyclohexyl)ethyl pivalate

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Chemical Property of 2-((1S,2S,5S,6S)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-oxocyclohexyl)ethyl pivalate

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Technology Process of 2-((1S,2S,5S,6S)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-oxocyclohexyl)ethyl pivalate

There total 26 articles about 2-((1S,2S,5S,6S)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-oxocyclohexyl)ethyl pivalate 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: 69.0%

: ethyl 2-((1S,2R,3S,Z)-2-((tert-butyldimethylsilyl)oxy)-3-methyl-5-oxo-6-(pyrrolidin-2-ylidene)cyclohexyl)acetate

: 762-72-1
allyl-trimethyl-silane

: 1417600-72-6
2-((1S,2S,5S,6S)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-oxocyclohexyl)ethyl pivalate

Guidance literature:: With ammonium cerium (IV) nitrate; In acetonitrile; at 0 ℃; diastereoselective reaction;
DOI:10.1021/jo302333s

Reference yield: 67.0%

: 2-((1S,2R,3S,Z)-2-((tert-butyldimethylsilyl)oxy)-3-methyl-5-oxo-6-(pyrrolidin-2-ylidene)cyclohexyl)ethyl pivalate

: 762-72-1
allyl-trimethyl-silane

: 1417601-00-3
C₂₇H₄₇NO₄Si

: 1417600-72-6
2-((1S,2S,5S,6S)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-oxocyclohexyl)ethyl pivalate

Guidance literature:: With ammonium cerium (IV) nitrate; In acetonitrile; at 0 ℃; for 0.166667h; Inert atmosphere;
DOI:10.1021/jo302333s

Reference yield:

: 1131783-48-6
(4R,5S,E)-ethyl 4-hydroxy-5-methylhepta-2,6-dienoate

: 1417600-72-6
2-((1S,2S,5S,6S)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-oxocyclohexyl)ethyl pivalate

Guidance literature:: Multi-step reaction with 7 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C

2: dimethyl sulfide borane; 2-methyl-but-2-ene / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere

3: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

4: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogen phosphate monohydrate / water; acetonitrile; tert-butyl alcohol / 3.5 h / 0 °C / Inert atmosphere

5: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane

6: ammonium cerium (IV) nitrate / water; acetonitrile / 0.08 h / 20 °C / Inert atmosphere

7: ammonium cerium (IV) nitrate / acetonitrile / 0 °C

With 1H-imidazole; sodium chlorite; ammonium cerium (IV) nitrate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; oxalyl dichloride; dimethyl sulfide borane; Dess-Martin periodane; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 6: |Michael Addition;
DOI:10.1021/jo302333s