(2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-[(p-nitrobenzoyl)oxy]butane

Base Information

• Chemical Name: (2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-[(p-nitrobenzoyl)oxy]butane
• CAS No.: 197714-16-2
• Molecular Formula: C₂₃H₃₁NO₅Si
• Molecular Weight: 429.588
• Mol file: 197714-16-2.mol

Synonyms:(2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-[(p-nitrobenzoyl)oxy]butane

Chemical Property of (2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-[(p-nitrobenzoyl)oxy]butane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-[(p-nitrobenzoyl)oxy]butane

There total 4 articles about (2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-[(p-nitrobenzoyl)oxy]butane 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: 51.0%

(2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol (197714-08-2) + 4-nitro-benzoic acid (62-23-7) → (2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-[(p-nitrobenzoyl)oxy]butane (197714-16-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In benzene; at 20 ℃; for 12h;

DOI:10.1021/jo971178f

Reference yield:

(2S,3S)-2,3-epoxy-3-phenyl-1-propanol (104196-23-8) → (2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-[(p-nitrobenzoyl)oxy]butane (197714-16-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: CuCN / diethyl ether / 1 h / -68 °C

1.2: 77 percent / diethyl ether / 3 h / -68 - 0 °C

2.1: 78 percent / imidazole / dimethylformamide / 24 h

3.1: 51 percent / PPh₃; diethyl azodicarboxylate / benzene / 12 h / 20 °C

With 1H-imidazole; triphenylphosphine; diethylazodicarboxylate; In diethyl ether; N,N-dimethyl-formamide; benzene; 1.1: transmetallation / 1.2: Ring cleavage / 2.1: silylation / 3.1: Mitsunobu reaction;

DOI:10.1021/jo971178f

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-[(p-nitrobenzoyl)oxy]butane (197714-16-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / imidazole / dimethylformamide / 24 h

2: 51 percent / PPh₃; diethyl azodicarboxylate / benzene / 12 h / 20 °C

With 1H-imidazole; triphenylphosphine; diethylazodicarboxylate; In N,N-dimethyl-formamide; benzene; 1: silylation / 2: Mitsunobu reaction;

DOI:10.1021/jo971178f

upstream raw materials:

(2R,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol

4-nitro-benzoic acid

(2S,3S)-2,3-epoxy-3-phenyl-1-propanol

tert-butyldimethylsilyl chloride

Downstream raw materials:

(2S,3R)-1-[(tert-butyldimethylsilyl)oxy]-3-phenyl-2-butanol

(2R,3R)-2-[(tert-butoxycarbonyl)amino]-3-phenylbutanoic acid

(2S,3R)-3-phenyl-2-(methanesulfonyloxy)-1-butanol

methyl (2S,3R)-2-(methanesulfonyloxy)-3-phenylbutanoate