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

Base Information

Chemical Name:2-((1S,2S,3R,5S,6R)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-3-hydroxy-5-methylcyclohexyl)ethyl pivalate
CAS No.:1417600-89-5
Molecular Formula:C₂₇H₄₉NO₄Si
Molecular Weight:479.776
Hs Code.:

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

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

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

There total 16 articles about 2-((1S,2S,3R,5S,6R)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-3-hydroxy-5-methylcyclohexyl)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: 55.0%

: 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

: 1417600-89-5
2-((1S,2S,3R,5S,6R)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-3-hydroxy-5-methylcyclohexyl)ethyl pivalate

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 20 ℃; for 72h; Inert atmosphere;
DOI:10.1021/jo302333s

Reference yield:

: 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

: 1417600-75-9
2-((1S,2S,3S,5S,6S)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-3-hydroxy-5-methylcyclohexyl)ethyl pivalate

: 1417600-89-5
2-((1S,2S,3R,5S,6R)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-3-hydroxy-5-methylcyclohexyl)ethyl pivalate

Guidance literature:: With tri-n-butyl-tin hydride; diethylaluminium chloride; In dichloromethane; at -78 - 20 ℃; Overall yield = 90 %;
DOI:10.1021/jo302333s

Reference yield:

: (E)-N-(1-(4-methoxyphenyl)ethylidene)pent-4-yn-1-amine

: 1417600-89-5
2-((1S,2S,3R,5S,6R)-2-allyl-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-3-hydroxy-5-methylcyclohexyl)ethyl pivalate

Guidance literature:: Multi-step reaction with 5 steps

1: 2,2'-azobis(isobutyronitrile) / benzine / 85 °C

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

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

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

5: sodium tetrahydroborate / tetrahydrofuran / 72 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; ammonium cerium (IV) nitrate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); N,N-dimethyl-formamide; In tetrahydrofuran; benzine; dichloromethane; water; acetonitrile; 3: |Michael Addition;
DOI:10.1021/jo302333s