(R)-4-benzyl-3-[(2S,3S)-2-azido-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)butyryl]oxazolidin-2-one

Base Information

Chemical Name:(R)-4-benzyl-3-[(2S,3S)-2-azido-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)butyryl]oxazolidin-2-one
CAS No.:506410-47-5
Molecular Formula:C₄₉H₅₂N₄O₈
Molecular Weight:824.974
Hs Code.:

Synonyms:(R)-4-benzyl-3-[(2S,3S)-2-azido-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)butyryl]oxazolidin-2-one

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Chemical Property of (R)-4-benzyl-3-[(2S,3S)-2-azido-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)butyryl]oxazolidin-2-one

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Technology Process of (R)-4-benzyl-3-[(2S,3S)-2-azido-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)butyryl]oxazolidin-2-one

There total 4 articles about (R)-4-benzyl-3-[(2S,3S)-2-azido-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)butyryl]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: 97.0%

: 506410-46-4
(R)-4-benzyl-3-[(2R,3S)-2-bromo-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)butyryl]oxazolidin-2-one

: 506410-47-5
(R)-4-benzyl-3-[(2S,3S)-2-azido-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)butyryl]oxazolidin-2-one

Guidance literature:: With tetramethylguanidinum azide; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1021/jo026758d

Reference yield:

: 40217-17-2,90719-32-7,120574-96-1,102029-44-7
(R)-4-(phenylmethyl)-2-oxazolidinone

: 506410-47-5
(R)-4-benzyl-3-[(2S,3S)-2-azido-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)butyryl]oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: Et₃N; pivaloyl chloride / tetrahydrofuran / 0.25 h / -78 °C

1.2: 79 percent / BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.1: diisopropylethylamine; Bu₂BOTf / CH₂Cl₂ / 1.25 h / -78 - 0 °C

2.2: 57 percent / NBS / CH₂Cl₂ / 2 h / -78 °C

3.1: 97 percent / tetramethylguanidinium azide / CH₂Cl₂ / 24 h / 20 °C

With di-n-butylboryl trifluoromethanesulfonate; pivaloyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; tetramethylguanidinum azide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo026758d

Reference yield:

: 506410-44-2
(S)-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)butyric acid

: 506410-47-5
(R)-4-benzyl-3-[(2S,3S)-2-azido-3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosylmethyl)butyryl]oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: Et₃N; pivaloyl chloride / tetrahydrofuran / 0.25 h / -78 °C

1.2: 79 percent / BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.1: diisopropylethylamine; Bu₂BOTf / CH₂Cl₂ / 1.25 h / -78 - 0 °C

2.2: 57 percent / NBS / CH₂Cl₂ / 2 h / -78 °C

3.1: 97 percent / tetramethylguanidinium azide / CH₂Cl₂ / 24 h / 20 °C

With di-n-butylboryl trifluoromethanesulfonate; pivaloyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; tetramethylguanidinum azide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo026758d