(4S)-4-benzyl-3-[(2R)-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-pent-4-enoyl]-oxazolidin-2-one

Base Information

Chemical Name:(4S)-4-benzyl-3-[(2R)-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-pent-4-enoyl]-oxazolidin-2-one
CAS No.:253450-80-5
Molecular Formula:C₂₉H₃₅NO₅
Molecular Weight:477.601
Hs Code.:

Synonyms:(4S)-4-benzyl-3-[(2R)-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-pent-4-enoyl]-oxazolidin-2-one

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Chemical Property of (4S)-4-benzyl-3-[(2R)-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-pent-4-enoyl]-oxazolidin-2-one

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Technology Process of (4S)-4-benzyl-3-[(2R)-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-pent-4-enoyl]-oxazolidin-2-one

There total 9 articles about (4S)-4-benzyl-3-[(2R)-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-pent-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: 71.0%

: 556-56-9
allyl iodid

: 253450-82-7
(4S)-4-benzyl-3-[2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-acetyl]-oxazolidin-2-one

: 253450-80-5
(4S)-4-benzyl-3-[(2R)-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-pent-4-enoyl]-oxazolidin-2-one

Guidance literature:: (4S)-4-benzyl-3-[2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-acetyl]-oxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

allyl iodid; In tetrahydrofuran; toluene; at -78 - -40 ℃; Further stages.;
DOI:10.1021/ol006091m

Reference yield: 71.0%

: 556-56-9
allyl iodid

: 253450-82-7
(4S)-4-benzyl-3-[2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-acetyl]-oxazolidin-2-one

: (4S)-4-benzyl-3-[(2S)-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-pent-4-enoyl]-oxazolidin-2-one

: 253450-80-5
(4S)-4-benzyl-3-[(2R)-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-pent-4-enoyl]-oxazolidin-2-one

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; toluene; at -45 ℃; for 0.5h;
DOI:10.1021/ol991201e

Reference yield:

: 88223-83-0
(3R,4R)-4-benzyloxy-hept-6-en-3-ol

: 253450-80-5
(4S)-4-benzyl-3-[(2R)-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-pent-4-enoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / sodium hydride / various solvent(s); tetrahydrofuran / 84 h / 20 °C

2: triethylamine / diethyl ether / 1 h / 0 °C

3: 1.16 g / n-butyl lithium / hexane; tetrahydrofuran / 1 h / 0 °C

4: 71 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 0.5 h / -45 °C

With n-butyllithium; sodium hexamethyldisilazane; sodium hydride; triethylamine; In tetrahydrofuran; diethyl ether; hexane; toluene;
DOI:10.1021/ol991201e