(S)-4-Benzyl-3-[(Z)-(2S,3R)-3-hydroxy-7-(4-methoxy-benzyloxy)-2,5-dimethyl-hept-4-enoyl]-oxazolidin-2-one

Base Information

Chemical Name:(S)-4-Benzyl-3-[(Z)-(2S,3R)-3-hydroxy-7-(4-methoxy-benzyloxy)-2,5-dimethyl-hept-4-enoyl]-oxazolidin-2-one
CAS No.:266675-80-3
Molecular Formula:C₂₇H₃₃NO₆
Molecular Weight:467.562
Hs Code.:

Synonyms:(S)-4-Benzyl-3-[(Z)-(2S,3R)-3-hydroxy-7-(4-methoxy-benzyloxy)-2,5-dimethyl-hept-4-enoyl]-oxazolidin-2-one

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Chemical Property of (S)-4-Benzyl-3-[(Z)-(2S,3R)-3-hydroxy-7-(4-methoxy-benzyloxy)-2,5-dimethyl-hept-4-enoyl]-oxazolidin-2-one

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Technology Process of (S)-4-Benzyl-3-[(Z)-(2S,3R)-3-hydroxy-7-(4-methoxy-benzyloxy)-2,5-dimethyl-hept-4-enoyl]-oxazolidin-2-one

There total 6 articles about (S)-4-Benzyl-3-[(Z)-(2S,3R)-3-hydroxy-7-(4-methoxy-benzyloxy)-2,5-dimethyl-hept-4-enoyl]-oxazolidin-2-one 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: 98.0%

: 131685-53-5,101711-78-8
(S)-4-benzyl-3-propionyl-2-oxazolidinone

: (Z)-5-((4-methoxybenzyl)oxy)-3-methylpent-2-enal

: 266675-80-3
(S)-4-Benzyl-3-[(Z)-(2S,3R)-3-hydroxy-7-(4-methoxy-benzyloxy)-2,5-dimethyl-hept-4-enoyl]-oxazolidin-2-one

Guidance literature:: (S)-4-benzyl-3-propionyl-2-oxazolidinone; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

(Z)-5-((4-methoxybenzyl)oxy)-3-methylpent-2-enal; In dichloromethane; at -78 ℃; for 2h; Inert atmosphere;

With dihydrogen peroxide; In methanol; aq. phosphate buffer; dichloromethane; at 0 ℃; for 0.5h; pH=7; Inert atmosphere;
DOI:10.1016/j.tet.2021.132354

Reference yield: 74.0%

: 131685-53-5,101711-78-8
(S)-4-benzyl-3-propionyl-2-oxazolidinone

: 266675-79-0
(Z)-5-(4-methoxybenzyloxy)-3-methylpent-2-en-1-ol

: 266675-80-3
(S)-4-Benzyl-3-[(Z)-(2S,3R)-3-hydroxy-7-(4-methoxy-benzyloxy)-2,5-dimethyl-hept-4-enoyl]-oxazolidin-2-one

Guidance literature:: (Z)-5-(4-methoxybenzyloxy)-3-methylpent-2-en-1-ol; With manganese(IV) oxide; In dichloromethane;

(S)-4-benzyl-3-propionyl-2-oxazolidinone; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 ℃; Further stages.;
DOI:10.1021/ol9904085

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 266675-80-3
(S)-4-Benzyl-3-[(Z)-(2S,3R)-3-hydroxy-7-(4-methoxy-benzyloxy)-2,5-dimethyl-hept-4-enoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: TfOH / diethyl ether / 20 °C

2.1: nBuLi / tetrahydrofuran / -78 - 20 °C

3.1: tetrahydrofuran / -45 °C

4.1: LiAlH₄ / diethyl ether / 0 °C

5.1: MnO₂ / CH₂Cl₂

5.2: 74 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; n-butyllithium; trifluorormethanesulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Substitution / 2.1: Substitution / 3.1: Addition / 4.1: Reduction / 5.1: Oxidation / 5.2: Evans aldolization;
DOI:10.1021/ol9904085