(+)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxytetradec-(1R)-hydroxy-2-enyl]-5-oxopyrrolidine-1-carboxylate

Base Information

Chemical Name:(+)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxytetradec-(1R)-hydroxy-2-enyl]-5-oxopyrrolidine-1-carboxylate
CAS No.:246545-53-9
Molecular Formula:C₃₈H₆₅NO₆Si₂
Molecular Weight:688.108
Hs Code.:

(+)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxytetradec-(1R)-hydroxy-2-enyl]-5-oxopyrrolidine-1-carboxylate

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

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

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

There total 5 articles about (+)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxytetradec-(1R)-hydroxy-2-enyl]-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:

: 3839-31-4
dimethyl(phenyl)silyllithium

: 81658-27-7
(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

: (E)-4,5-epoxytetradec-2-enal

: (-)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4S,5S)-epoxytetradec-(1R)-hydroxy-2-enyl]-5-oxopyrrolidine-1-carboxylate

: 246545-53-9
(+)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxytetradec-(1R)-hydroxy-2-enyl]-5-oxopyrrolidine-1-carboxylate

Guidance literature:: dimethyl(phenyl)silyllithium; (S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate; With diethylzinc; In tetrahydrofuran; at -78 ℃;

(E)-4,5-epoxytetradec-2-enal; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1021/jo9905672

Reference yield:

: α-oxiranyldodecanal

: 246545-53-9
(+)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxytetradec-(1R)-hydroxy-2-enyl]-5-oxopyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / NaH / tetrahydrofuran / -78 - 25 °C

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

3.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

4.1: Et₂Zn / tetrahydrofuran / -78 °C

4.2: tetrahydrofuran / -78 - 20 °C

With diethylzinc; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Condensation / 2.1: Reduction / 3.1: Oxidation / 4.1: Addition / 4.2: Addition;
DOI:10.1021/jo9905672

Reference yield:

: 123932-69-4,246545-38-0
(3-nonyloxiran-2-yl)methanol

: 246545-53-9
(+)-tert-butyl (2R,3S,4R)-2-[(tert-butyldimethylsiloxy)methyl]-3-(dimethylphenylsilyl)-4-[(E)-(4R,5R)-epoxytetradec-(1R)-hydroxy-2-enyl]-5-oxopyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 25 °C

2.1: 92 percent / NaH / tetrahydrofuran / -78 - 25 °C

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

4.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

5.1: Et₂Zn / tetrahydrofuran / -78 °C

5.2: tetrahydrofuran / -78 - 20 °C

With diethylzinc; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Oxidation / 2.1: Condensation / 3.1: Reduction / 4.1: Oxidation / 5.1: Addition / 5.2: Addition;
DOI:10.1021/jo9905672