(4R) 4-benzyl-3-[2-(1'S,2R,4E)-(1'-methoxymethoxy-hexyl)-4-methyl-5-(trimethylsilanyl)-pent-4-enoyl]-oxazolidin-2-one

Base Information

Chemical Name:(4R) 4-benzyl-3-[2-(1'S,2R,4E)-(1'-methoxymethoxy-hexyl)-4-methyl-5-(trimethylsilanyl)-pent-4-enoyl]-oxazolidin-2-one
CAS No.:500795-33-5
Molecular Formula:C₂₇H₄₃NO₅Si
Molecular Weight:489.728
Hs Code.:

Synonyms:(4R) 4-benzyl-3-[2-(1'S,2R,4E)-(1'-methoxymethoxy-hexyl)-4-methyl-5-(trimethylsilanyl)-pent-4-enoyl]-oxazolidin-2-one

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Chemical Property of (4R) 4-benzyl-3-[2-(1'S,2R,4E)-(1'-methoxymethoxy-hexyl)-4-methyl-5-(trimethylsilanyl)-pent-4-enoyl]-oxazolidin-2-one

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Technology Process of (4R) 4-benzyl-3-[2-(1'S,2R,4E)-(1'-methoxymethoxy-hexyl)-4-methyl-5-(trimethylsilanyl)-pent-4-enoyl]-oxazolidin-2-one

There total 2 articles about (4R) 4-benzyl-3-[2-(1'S,2R,4E)-(1'-methoxymethoxy-hexyl)-4-methyl-5-(trimethylsilanyl)-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:

: 107-30-2
chloromethyl methyl ether

: (4R)-4-benzyl-3-[(2R)-2-(2-methyl-3-trimethylsilyl-E-2-propen-1-yl)-3-hydroxyoctanoyl]oxazolidin-2-one

: 500795-33-5
(4R) 4-benzyl-3-[2-(1'S,2R,4E)-(1'-methoxymethoxy-hexyl)-4-methyl-5-(trimethylsilanyl)-pent-4-enoyl]-oxazolidin-2-one

: (4R)-4-benzyl-3-[2-(1'R,2R,4E)-(1'-methoxymethoxyhexyl)-4-methyl-5-(trimethylsilanyl)pent-4-enoyl]oxazolidin-2-one

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1.5h;
DOI:10.1021/ja048493l

Reference yield:

: 107-30-2
chloromethyl methyl ether

: 327165-41-3
(4R)-4-benzyl-3-[(2R,3S)-2-(2-methyl-3-trimethylsilyl-E-2-propen-1-yl)-3-hydroxyoctanoyl]-oxazolidin-2-one

: 500795-33-5
(4R) 4-benzyl-3-[2-(1'S,2R,4E)-(1'-methoxymethoxy-hexyl)-4-methyl-5-(trimethylsilanyl)-pent-4-enoyl]-oxazolidin-2-one

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1.5h;
DOI:10.1021/ol027569k

Reference yield:

: 500795-33-5
(4R) 4-benzyl-3-[2-(1'S,2R,4E)-(1'-methoxymethoxy-hexyl)-4-methyl-5-(trimethylsilanyl)-pent-4-enoyl]-oxazolidin-2-one

: {(E)-(4R,5S)-5-Methoxymethoxy-4-[(4S,5S)-2-(4-methoxy-phenyl)-5-methyl-5-((Z)-propenyl)-[1,3]dioxolan-4-yl]-2-methyl-dec-1-enyl}-trimethyl-silane

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / lithium borohydride / diethyl ether; ethanol; tetrahydrofuran / 4 h / 0 °C

2: oxalyl chloride; dimethyl sulfoxide; Et₃N / CH₂Cl₂ / -70 - 0 °C

3: tetrahydrofuran; pentane / 0.17 h / -118 °C

4: 72 percent / potassium hexamethyldisilazide; triethylamine / tetrahydrofuran / 1 h / 0 °C

5: 97 percent / aq. hydrochloric acid / tetrahydrofuran / 0.33 h / 23 °C

6: 94 percent / tetrahydrofuran / -45 - -30 °C

7: 75 percent / DDQ / CH₂Cl₂ / 0 °C

8: 78 percent / hydrogen; quinoline / Lindlar's catalyst / ethyl acetate / 20 °C

With quinoline; hydrogenchloride; lithium borohydride; oxalyl dichloride; hydrogen; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; pentane; 2: Swern oxidation;
DOI:10.1021/ol027569k