(S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)oxazolidin-2-one

Base Information

Chemical Name:(S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)oxazolidin-2-one
CAS No.:918310-84-6
Molecular Formula:C₁₉H₂₅NO₃Si
Molecular Weight:343.498
Hs Code.:

Synonyms:(S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)oxazolidin-2-one

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Chemical Property of (S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)oxazolidin-2-one

Chemical Property:

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Technology Process of (S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)oxazolidin-2-one

There total 1 articles about (S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)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: 85.0%

: 78199-88-9
3-iodo-1-propynyl(trimethyl)silane

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

: 918310-84-6
(S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)oxazolidin-2-one

Guidance literature:: (S)-4-benzyl-3-propionyl-2-oxazolidinone; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;

3-iodo-1-propynyl(trimethyl)silane; In tetrahydrofuran; for 1h;
DOI:10.1021/ja066971h

Reference yield:

: 918310-84-6
(S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)oxazolidin-2-one

: 918310-78-8
(2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 79 percent / LiBH₄; H₂O / diethyl ether / 0.83 h / 0 °C

2.1: 89 percent / imidazole; triphenyl phosphine; I₂ / CH₂Cl₂ / 3.5 h

3.1: tert-butyllithium / pentane; diethyl ether / 0.08 h / -78 °C

3.2: 90 percent / pentane; diethyl ether / 1 h

4.1: 70 percent / diisopropylethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 1.5 h / 0 °C

5.1: LiI / diethyl ether / 0.08 h / -40 °C

5.2: LiAlH₄ / diethyl ether / 2 h / -100 °C

6.1: 96 percent / imidazole; DMAP / CH₂Cl₂ / 12 h

7.1: 69 percent / pyridine; HF*pyridine / tetrahydrofuran / 3.5 h / 20 °C

8.1: 100 percent / diisopropylethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.75 h / 0 °C

9.1: 148 mg / MgBr₂*OEt₂ / CH₂Cl₂ / 12 h / -78 - 20 °C

10.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium borohydride; pyridine-SO₃ complex; water; iodine; tert.-butyl lithium; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; magnesium bromide; lithium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; pentane; 9.1: Mukaiyama aldol reaction;
DOI:10.1021/ja066971h

Reference yield:

: 918310-84-6
(S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)oxazolidin-2-one

: 896730-06-6
(2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-ynal

Guidance literature:: Multi-step reaction with 8 steps

1.1: 79 percent / LiBH₄; H₂O / diethyl ether / 0.83 h / 0 °C

2.1: 89 percent / imidazole; triphenyl phosphine; I₂ / CH₂Cl₂ / 3.5 h

3.1: tert-butyllithium / pentane; diethyl ether / 0.08 h / -78 °C

3.2: 90 percent / pentane; diethyl ether / 1 h

4.1: 70 percent / diisopropylethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 1.5 h / 0 °C

5.1: LiI / diethyl ether / 0.08 h / -40 °C

5.2: LiAlH₄ / diethyl ether / 2 h / -100 °C

6.1: 96 percent / imidazole; DMAP / CH₂Cl₂ / 12 h

7.1: 69 percent / pyridine; HF*pyridine / tetrahydrofuran / 3.5 h / 20 °C

8.1: 100 percent / diisopropylethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.75 h / 0 °C

With pyridine; 1H-imidazole; dmap; lithium borohydride; pyridine-SO₃ complex; water; iodine; tert.-butyl lithium; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; pentane;
DOI:10.1021/ja066971h