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

Base Information

• Chemical Name: N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-hydroxybutanamide
• CAS No.: 1335286-69-5
• Molecular Formula: C₃₂H₄₁NO₃Si
• Molecular Weight: 515.768

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 8 articles about N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-hydroxybutanamide 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: 76.0%

N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-tert-butyldimethylsilyloxy-butanamide (1335286-68-4) → N-benzyl-N-[(1R,2S)-2-tert-butyldiphenylsilyloxy-1-methyl-3-butenyl]-(S)-3-hydroxybutanamide (1335286-69-5)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2011.08.014

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-hydroxybutanamide (1335286-69-5)

Guidance literature:

Multi-step reaction with 4 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

4.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 20 °C / Inert atmosphere

With dmap; 2-picoline borane complex; tetrabutyl ammonium fluoride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; 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-hydroxybutanamide (1335286-69-5)

Guidance literature:

Multi-step reaction with 3 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

3: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 20 °C / Inert atmosphere

With dmap; 2-picoline borane complex; tetrabutyl ammonium fluoride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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

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

C₂₈H₃₅NOSi

Downstream raw materials:

(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

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

(3S,6E,8R,9S,12E,14R,15S)-16-benzyl-14-hydroxy-8-(2-methoxyethoxy)methoxy-3,9,15-trimethyl-16-aza-4,10-dioxa-6,12-cyclohexadecadiene-1,5,11-trione

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