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

Base Information

Chemical Name:2-((1S,2S,3S,5S,6S)-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-3-hydroxy-2-(3-hydroxypropyl)-5-methylcyclohexyl)ethyl pivalate
CAS No.:1417600-77-1
Molecular Formula:C₂₇H₅₁NO₅Si
Molecular Weight:497.791
Hs Code.:

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

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

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

There total 16 articles about 2-((1S,2S,3S,5S,6S)-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-3-hydroxy-2-(3-hydroxypropyl)-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: 28.0%

: 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

: 1417600-77-1
2-((1S,2S,3S,5S,6S)-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-3-hydroxy-2-(3-hydroxypropyl)-5-methylcyclohexyl)ethyl pivalate

Guidance literature:: With dimethyl sulfide borane; In tetrahydrofuran; at 0 ℃; for 3.5h; Inert atmosphere;
DOI:10.1021/jo302333s

Reference yield:

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

: 1417600-77-1
2-((1S,2S,3S,5S,6S)-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-3-hydroxy-2-(3-hydroxypropyl)-5-methylcyclohexyl)ethyl pivalate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 2,2'-azobis(isobutyronitrile) / benzine / 85 °C

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

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

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

5.1: diethylaluminium chloride / dichloromethane; toluene / 0.5 h / -78 °C / Inert atmosphere

5.2: 3.5 h / -78 - 20 °C / Inert atmosphere

6.1: dimethyl sulfide borane / tetrahydrofuran / 3.5 h / 0 °C / Inert atmosphere

With ammonium cerium (IV) nitrate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); dimethyl sulfide borane; diethylaluminium chloride; N,N-dimethyl-formamide; In tetrahydrofuran; benzine; dichloromethane; water; toluene; acetonitrile; 3.1: |Michael Addition;
DOI:10.1021/jo302333s

Reference yield:

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

: 1417600-77-1
2-((1S,2S,3S,5S,6S)-6-((tert-butyldimethylsilyl)oxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-3-hydroxy-2-(3-hydroxypropyl)-5-methylcyclohexyl)ethyl pivalate

Guidance literature:: Multi-step reaction with 11 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C

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

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

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

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

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

7.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / 0 - 20 °C / Inert atmosphere

8.1: dmap; triethylamine / dichloromethane / 40 h / 20 °C / Inert atmosphere

9.1: ammonium cerium (IV) nitrate / acetonitrile / 0.17 h / 0 °C / Inert atmosphere

10.1: diethylaluminium chloride / dichloromethane; toluene / 0.5 h / -78 °C / Inert atmosphere

10.2: 3.5 h / -78 - 20 °C / Inert atmosphere

11.1: dimethyl sulfide borane / tetrahydrofuran / 3.5 h / 0 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium chlorite; ammonium cerium (IV) nitrate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; oxalyl dichloride; dimethyl sulfide borane; diethylaluminium chloride; Dess-Martin periodane; triethylamine; N,N-dimethyl-formamide; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 6.1: |Michael Addition;
DOI:10.1021/jo302333s