tert-butyl (2R)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(triphenylmethylsulfenyl)amino]pentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

Base Information

Chemical Name:tert-butyl (2R)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(triphenylmethylsulfenyl)amino]pentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate
CAS No.:335693-23-7
Molecular Formula:C₃₅H₄₂N₂O₄S
Molecular Weight:586.795
Hs Code.:

Synonyms:tert-butyl (2R)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(triphenylmethylsulfenyl)amino]pentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

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Chemical Property of tert-butyl (2R)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(triphenylmethylsulfenyl)amino]pentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

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Technology Process of tert-butyl (2R)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(triphenylmethylsulfenyl)amino]pentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

There total 14 articles about tert-butyl (2R)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(triphenylmethylsulfenyl)amino]pentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 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: 85.2%

: 141293-28-9
N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole

: 408505-13-5
(2S)-2-methoxy-2-methyl-pentylidene-N-triphenylmethylsulfenamide

: 408505-14-6
tert-butyl (2S)-2-((1S,2S)-2-methoxy-2-methyl-1-((tritylsulfenyl)amino)pentyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

: 335693-23-7
tert-butyl (2R)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(triphenylmethylsulfenyl)amino]pentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

Guidance literature:: With trifluorormethanesulfonic acid; In tetrahydrofuran; at -45 - -35 ℃; for 3.5h;
DOI:10.1016/S0957-4166(03)00597-4

Reference yield: 52.0%

: 141293-28-9
N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole

: 471257-47-3
(1E,2S)-2-methoxy-2-methylpentanal S-tritylthioxime

: 408505-14-6
tert-butyl (2S)-2-((1S,2S)-2-methoxy-2-methyl-1-((tritylsulfenyl)amino)pentyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

: 335693-23-7
tert-butyl (2R)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(triphenylmethylsulfenyl)amino]pentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

Guidance literature:: With boron trifluoride diethyl etherate; In diethyl ether; at -78 - -50 ℃; for 3h;
DOI:10.1021/jo0162890

Reference yield:

: 16958-19-3
(2E)-2-methyl-2-penten-1-ol

: 335693-23-7
tert-butyl (2R)-2-{(1R,2S)-2-methoxy-2-methyl-1-[(triphenylmethylsulfenyl)amino]pentyl}-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: (-)-dimethyl D-tartrate; titanium tetraisopropoxide; tert-butylhydroperoxide / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 4 h / -20 °C

2: 7.35 g / trimethylphosphite; triethylamine / CH₂Cl₂; decane / 1.5 h

3: 63 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 °C

4: 98 percent / sodium hydride / tetrahydrofuran / 16 h / 0 - 20 °C

5: 98 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 16 h / 0 - 20 °C

6: hydrogen / 20percent Pd(OH)2 on carbon / CH₂Cl₂ / 3.5 h

7: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH₂Cl₂ / 1.5 h / 20 °C

8: pyridinium p-toluenesulfonate; MgSO₄ / diethyl ether / 18 h / 20 °C

9: 52 percent / BF₃*Et₂O / diethyl ether / 3 h / -78 - -50 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; Dimethyl D-tartrate; 4 A molecular sieve; Celite; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; magnesium sulfate; triethylamine; pyridinium chlorochromate; phosphorous acid trimethyl ester; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; decane; dichloromethane;
DOI:10.1021/jo0162890