(2R,3S)-7-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-heptan-1-one

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Chemical Name:(2R,3S)-7-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-heptan-1-one
CAS No.:906067-07-0
Molecular Formula:C₂₅H₃₁NO₄S
Molecular Weight:441.591
Hs Code.:

Synonyms:(2R,3S)-7-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-heptan-1-one

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Chemical Property of (2R,3S)-7-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-heptan-1-one

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Technology Process of (2R,3S)-7-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-heptan-1-one

There total 1 articles about (2R,3S)-7-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-heptan-1-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: 78.0%

: 78999-24-3
5-benzyloxy-1-pentanal

: 145588-95-0,334968-78-4
N-propanoyl-(S)-4-benzyl-1,3-oxazolidine-2-thione

: 906067-07-0
(2R,3S)-7-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-heptan-1-one

Guidance literature:: N-propanoyl-(S)-4-benzyl-1,3-oxazolidine-2-thione; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 0.25h;

5-benzyloxy-1-pentanal; In dichloromethane; at -78 - 0 ℃; for 3h;
DOI:10.1016/j.tetlet.2006.05.113

Reference yield:

: 906067-07-0
(2R,3S)-7-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-heptan-1-one

: 906067-10-5
(R)-4-Benzyl-3-[(5S,6S)-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 90 percent / NaBH₄ / ethanol / 0.17 h / 0 °C

2.1: imidazole; DMAP / dimethylformamide / 24 h / 0 - 20 °C

3.1: H₂ / Pd/C / ethyl acetate

4.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0 - 20 °C

5.1: Piv-Cl; Et₃N / tetrahydrofuran

5.2: 85 percent / LiCl / tetrahydrofuran / 4 h / -20 - 20 °C

With 1H-imidazole; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; hydrogen; pivaloyl chloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 4.1: Swern oxidation;
DOI:10.1016/j.tetlet.2006.05.113

Reference yield:

: 906067-07-0
(2R,3S)-7-Benzyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-2-methyl-heptan-1-one

: (R)-4-Benzyl-3-[(2R,5S,6S)-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-heptanoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / NaBH₄ / ethanol / 0.17 h / 0 °C

2.1: imidazole; DMAP / dimethylformamide / 24 h / 0 - 20 °C

3.1: H₂ / Pd/C / ethyl acetate

4.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0 - 20 °C

5.1: Piv-Cl; Et₃N / tetrahydrofuran

5.2: 85 percent / LiCl / tetrahydrofuran / 4 h / -20 - 20 °C

6.1: NaHMDS / tetrahydrofuran / 2 h / -78 °C

With 1H-imidazole; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; hydrogen; sodium hexamethyldisilazane; pivaloyl chloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 4.1: Swern oxidation;
DOI:10.1016/j.tetlet.2006.05.113