(-)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxytetradec-(1R)-hydroxy-2-en-1-yl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-1-carboxylate

Base Information

Chemical Name:(-)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxytetradec-(1R)-hydroxy-2-en-1-yl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-1-carboxylate
CAS No.:222847-80-5
Molecular Formula:C₄₄H₆₉NO₇Si₂
Molecular Weight:780.205
Hs Code.:

(-)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxytetradec-(1R)-hydroxy-2-en-1-yl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-1-carboxylate

Synonyms:(-)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxytetradec-(1R)-hydroxy-2-en-1-yl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-1-carboxylate

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Chemical Property of (-)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxytetradec-(1R)-hydroxy-2-en-1-yl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-1-carboxylate

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Technology Process of (-)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxytetradec-(1R)-hydroxy-2-en-1-yl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-1-carboxylate

There total 11 articles about (-)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxytetradec-(1R)-hydroxy-2-en-1-yl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-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:

: 64-17-5
ethanol

: (2R,3S,4R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(diethylamino-diphenyl-silanyl)-4-[(E)-(R)-1-hydroxy-3-((2S,3S)-3-nonyl-oxiranyl)-allyl]-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: 222847-80-5
(-)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxytetradec-(1R)-hydroxy-2-en-1-yl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-1-carboxylate

Guidance literature:: With ammonium chloride; for 24h;
DOI:10.1039/a807988i

Reference yield:

: 246545-41-5
(+)-(2R,3S)-2,3-epoxydodecanal

: 222847-80-5
(-)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxytetradec-(1R)-hydroxy-2-en-1-yl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / toluene / 12 h / Heating

2: Et₂Zn / tetrahydrofuran / -78 - 20 °C

3: NH₄Cl / tetrahydrofuran / 12 h / 20 °C

With diethylzinc; ammonium chloride; In tetrahydrofuran; toluene; 1: Condensation / 2: Addition / 3: Substitution;
DOI:10.1021/jo9905672

Reference yield:

: (-)-(2S,3R)-2,3-epoxydodecanal

: 222847-80-5
(-)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxytetradec-(1R)-hydroxy-2-en-1-yl]-3-(ethoxydiphenylsilyl)-5-oxopyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: NaH / tetrahydrofuran / -78 - 25 °C

2: DIBAl-H / diethyl ether / -78 - 25 °C

3: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

4: Et₂Zn / tetrahydrofuran / -78 - 20 °C

5: NH₄Cl / tetrahydrofuran / 12 h / 20 °C

With diethylzinc; sodium hydride; diisobutylaluminium hydride; ammonium chloride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Condensation / 2: Reduction / 3: Oxidation / 4: Addition / 5: Substitution;
DOI:10.1021/jo9905672