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

Base Information

Chemical Name:(-)-tert-butyl (2R,3R,4R)-2[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxy-1-oxotetradec-2-en-1-yl]-3-(ethoxydiphenylsilyl)-4-hydroxy-5-oxopyrrolidine-1-carboxylate
CAS No.:222847-93-0
Molecular Formula:C₄₄H₆₇NO₈Si₂
Molecular Weight:794.189
Hs Code.:

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

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

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

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

There total 14 articles about (-)-tert-butyl (2R,3R,4R)-2[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxy-1-oxotetradec-2-en-1-yl]-3-(ethoxydiphenylsilyl)-4-hydroxy-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:

: 222847-85-0
(2R,3S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(ethoxy-diphenyl-silanyl)-4-[(E)-1-hydroxy-3-((2S,3S)-3-nonyl-oxiranyl)-prop-2-en-(E)-ylidene]-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

: 222847-93-0
(-)-tert-butyl (2R,3R,4R)-2[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxy-1-oxotetradec-2-en-1-yl]-3-(ethoxydiphenylsilyl)-4-hydroxy-5-oxopyrrolidine-1-carboxylate

Guidance literature:: With 2-methyl-1,2-epoxypropane; bis(acetylacetonate)nickel(II); In water; acetone; at 0 ℃; Yield given;
DOI:10.1039/a807988i

Reference yield:

: 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

: 222847-93-0
(-)-tert-butyl (2R,3R,4R)-2[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxy-1-oxotetradec-2-en-1-yl]-3-(ethoxydiphenylsilyl)-4-hydroxy-5-oxopyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

2: aq. Ni(acac)2 / acetone / 2.5 h / 0 - 20 °C

With bis(acetylacetonate)nickel(II); Dess-Martin periodane; In dichloromethane; acetone; 1: Oxidation / 2: hydroxylation;
DOI:10.1021/jo9905672

Reference yield:

: (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

: 222847-93-0
(-)-tert-butyl (2R,3R,4R)-2[(tert-butyldimethylsiloxy)methyl]-4-[(E)-(4S,5S)-epoxy-1-oxotetradec-2-en-1-yl]-3-(ethoxydiphenylsilyl)-4-hydroxy-5-oxopyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: aq. Ni(acac)2 / acetone / 2.5 h / 0 - 20 °C

With bis(acetylacetonate)nickel(II); ammonium chloride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; acetone; 1: Substitution / 2: Oxidation / 3: hydroxylation;
DOI:10.1021/jo9905672