N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-tert-butyldimethylsilyloxy-butanamide

Base Information

• Chemical Name: N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-tert-butyldimethylsilyloxy-butanamide
• CAS No.: 1335286-68-4
• Molecular Formula: C₃₈H₅₅NO₃Si₂
• Molecular Weight: 630.031

Synonyms:N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-tert-butyldimethylsilyloxy-butanamide

Chemical Property of N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-tert-butyldimethylsilyloxy-butanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-tert-butyldimethylsilyloxy-butanamide

There total 8 articles about N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-tert-butyldimethylsilyloxy-butanamide 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:

N-(tert-butoxycarbonyl)-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]amine (1335286-67-3) → N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-tert-butyldimethylsilyloxy-butanamide (1335286-68-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

1.2: Inert atmosphere; Saturated solution

2.1: 2-picoline borane complex; acetic acid / methanol / 0.5 h / 0 - 20 °C / Inert atmosphere

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C / Inert atmosphere

With dmap; 2-picoline borane complex; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1016/j.tet.2011.08.014

Reference yield:

C21H29NOSi (1357002-61-9) → N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-tert-butyldimethylsilyloxy-butanamide (1335286-68-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 2-picoline borane complex; acetic acid / methanol / 0.5 h / 0 - 20 °C / Inert atmosphere

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C / Inert atmosphere

With dmap; 2-picoline borane complex; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; dichloromethane;

DOI:10.1016/j.tet.2011.08.014

Reference yield:

C17H23NO4 → N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-tert-butyldimethylsilyloxy-butanamide (1335286-68-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: water; sodium hydroxide / tetrahydrofuran; methanol

2.1: dmap; triethylamine / 48 h / 0 - 90 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

3.2: Inert atmosphere; Saturated solution

4.1: 2-picoline borane complex; acetic acid / methanol / 0.5 h / 0 - 20 °C / Inert atmosphere

5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C / Inert atmosphere

With dmap; 2-picoline borane complex; water; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tet.2011.08.014

upstream raw materials:

N-(tert-butoxycarbonyl)-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]amine

C₂₁H₂₉NOSi

(2S,3R)-tert-butyl-N-(3-hydroxypent-4-en-2-yl)carbamate

tert-butyldimethylsilyl chloride

Downstream raw materials:

N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-hydroxybutanamide

(S)-3-{N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methylbutenyl]amino}-1-methyl-3-oxo-propyl (2E,4R,5S)-5-tert-butyldiphenylsilyloxy-4-(2-methoxyethoxy)methoxy-2-hexenoate

(S)-3-{N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methylbutenyl]amino}-1-methyl-3-oxo-propyl (2E,4R,5S)-5-hydroxy-4-(2-methoxyethoxy)methoxy-2-hexenoate

(S)-3-{N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methylbutenyl]amino}-1-methyl-3-oxo-propyl (2E,4R,5S)-5-acryloyloxy-4-(2-methoxyethoxy)methoxy-2-hexenoate

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