(4R)-4-benzyl-3-[(2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentanoyl]-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4R)-4-benzyl-3-[(2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentanoyl]-1,3-oxazolidin-2-one
• CAS No.: 591770-16-0
• Molecular Formula: C₂₈H₄₉NO₅Si₂
• Molecular Weight: 535.872

Synonyms:(4R)-4-benzyl-3-[(2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentanoyl]-1,3-oxazolidin-2-one

Chemical Property of (4R)-4-benzyl-3-[(2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentanoyl]-1,3-oxazolidin-2-one

Chemical Property:

Purity/Quality:

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Technology Process of (4R)-4-benzyl-3-[(2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentanoyl]-1,3-oxazolidin-2-one

There total 4 articles about (4R)-4-benzyl-3-[(2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentanoyl]-1,3-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: 93.0%

t-butyldimethylsiyl triflate (69739-34-0) + (4R)-4-benzyl-3-[(2R,3S)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methylpentanoyl]-1,3-oxazolidin-2-one (591770-15-9) → (4R)-4-benzyl-3-[(2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentanoyl]-1,3-oxazolidin-2-one (591770-16-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 23 ℃; for 12h;

DOI:10.1055/s-2003-40210

Reference yield: 90.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (4R)-4-benzyl-3-[(2R,3S)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methylpentanoyl]-1,3-oxazolidin-2-one (591770-15-9) → (4R)-4-benzyl-3-[(2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentanoyl]-1,3-oxazolidin-2-one (591770-16-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2006.06.173

Reference yield:

3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) → (4R)-4-benzyl-3-[(2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentanoyl]-1,3-oxazolidin-2-one (591770-16-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / Bu₂BOTf; DIPEA

2: 90 percent / imidazole / dimethylformamide

With 1H-imidazole; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; 1: Evans aldol condensation;

DOI:10.1016/j.tetlet.2006.06.173

upstream raw materials:

t-butyldimethylsiyl triflate

(4R)-4-benzyl-3-[(2R,3S)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methylpentanoyl]-1,3-oxazolidin-2-one

tert-butyldimethylsilyl chloride

3-(tert-butyldimethylsilanyloxy)propionaldehyde

Downstream raw materials:

C₂₂H₃₅NO₅Si

5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfonyl}-1-phenyl-1H-tetrazole

5-{[(2S,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methylpentyl]-sulfanyl}-1-phenyl-1H-tetrazole

{(1E,3R,4S)-4,6-bis{[(tert-butyl)dimethylsilyl]oxy}-3-methylhex-1-enyl}benzene

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