(2S,3S)-2-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide

Base Information

• Chemical Name: (2S,3S)-2-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide
• CAS No.: 1643654-99-2
• Molecular Formula: C₂₀H₃₄N₂O₅Si
• Molecular Weight: 410.586

Synonyms:(2S,3S)-2-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide

Chemical Property of (2S,3S)-2-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide

Chemical Property:

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Technology Process of (2S,3S)-2-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide

There total 2 articles about (2S,3S)-2-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide 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: 62.0%

(2S,3S)-2-((R)-1-hydroxyethyl)-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide (1643654-98-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3S)-2-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide (1643654-99-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 48h;

DOI:10.1002/chem.201402192

Reference yield:

(2S,3S)-2-acetyl-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide (1643654-76-5) → (2S,3S)-2-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide (1643654-99-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetramethylammonium borohydride / methanol / 4 h / -40 °C

2: 1H-imidazole / dichloromethane / 48 h / 0 - 20 °C

With 1H-imidazole; tetramethylammonium borohydride; In methanol; dichloromethane;

DOI:10.1002/chem.201402192

Reference yield: 65.0%

(2S,3S)-2-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide (1643654-99-2) → (R,E)-2-(2-nitro-1-phenylethyl)but-2-enal + (2S,3S)-2-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-nitro-3-phenylbutanal (1643654-97-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -40 - 0 ℃; for 3h;

DOI:10.1002/chem.201402192

upstream raw materials:

(2S,3S)-2-((R)-1-hydroxyethyl)-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide

tert-butyldimethylsilyl chloride

(2S,3S)-2-acetyl-N-methoxy-N-methyl-4-nitro-3-phenylbutanamide

Downstream raw materials:

(2S,3S)-2-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-nitro-3-phenylbutanal

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