(S)-4-benzyl-3-((S)-2-((S)-2-((tert-butyldimethylsilyl)oxy)-1-hydroxyethyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

Base Information

Chemical Name:(S)-4-benzyl-3-((S)-2-((S)-2-((tert-butyldimethylsilyl)oxy)-1-hydroxyethyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one
CAS No.:1449117-83-2
Molecular Formula:C₂₄H₃₇NO₅Si
Molecular Weight:447.647
Hs Code.:

Synonyms:(S)-4-benzyl-3-((S)-2-((S)-2-((tert-butyldimethylsilyl)oxy)-1-hydroxyethyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

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Chemical Property of (S)-4-benzyl-3-((S)-2-((S)-2-((tert-butyldimethylsilyl)oxy)-1-hydroxyethyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

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Technology Process of (S)-4-benzyl-3-((S)-2-((S)-2-((tert-butyldimethylsilyl)oxy)-1-hydroxyethyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

There total 1 articles about (S)-4-benzyl-3-((S)-2-((S)-2-((tert-butyldimethylsilyl)oxy)-1-hydroxyethyl)but-3-enoyl)-5,5-dimethyloxazolidin-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: 78.42%

: C₁₆H₁₉NO₃

: 102191-92-4
tert-butyldimethylsiloxyacetaldehyde

: 1449117-83-2
(S)-4-benzyl-3-((S)-2-((S)-2-((tert-butyldimethylsilyl)oxy)-1-hydroxyethyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

Guidance literature:: C₁₆H₁₉NO₃; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;

tert-butyldimethylsiloxyacetaldehyde; In dichloromethane; at -78 - 0 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol4019562

Reference yield: 80.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 1449117-83-2
(S)-4-benzyl-3-((S)-2-((S)-2-((tert-butyldimethylsilyl)oxy)-1-hydroxyethyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

: 1449117-84-3
(S)-4-benzyl-5,5-dimethyl-3-((S)-2-((S)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)but-3-enoyl)oxazolidin-2-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ol4019562 DOI:10.1021/ol500159h

Reference yield:

: 1449117-83-2
(S)-4-benzyl-3-((S)-2-((S)-2-((tert-butyldimethylsilyl)oxy)-1-hydroxyethyl)but-3-enoyl)-5,5-dimethyloxazolidin-2-one

: 1449117-97-8
(6aR,10aS)-di-tert-butyl 9-((S)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecan-5-yl)-6,6a-dihydroindolo[4,3-fg]quinoline-4,7(8H,10aH)-dicarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere

2: diisobutylaluminium hydride / dichloromethane; hexane / 0.33 h / -78 °C / Inert atmosphere

3: acetic acid; sodium cyanoborohydride / ethanol / 4 h / 80 °C / Inert atmosphere

4: sodium hydrogencarbonate / dichloromethane; water / 8 h / 20 °C

5: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 80 °C / Inert atmosphere

6: tetrakis(triphenylphosphine) palladium⁽⁰⁾; silver carbonate / toluene / 4 h / 100 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisobutylaluminium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; silver carbonate; In ethanol; hexane; dichloromethane; water; toluene; 6: |Heck Reaction;
DOI:10.1021/ol4019562