(4R,5S)-5-(tert-butyldiphenylsilyloxymethyl)-1-oxa-3-azabicyclo<3.1.0>hexan-2-one

Base Information

• Chemical Name: (4R,5S)-5-(tert-butyldiphenylsilyloxymethyl)-1-oxa-3-azabicyclo<3.1.0>hexan-2-one
• CAS No.: 223763-54-0
• Molecular Formula: C₂₁H₂₅NO₃Si
• Molecular Weight: 367.52
• Mol file: 223763-54-0.mol

Synonyms:(4R,5S)-5-(tert-butyldiphenylsilyloxymethyl)-1-oxa-3-azabicyclo<3.1.0>hexan-2-one

Chemical Property of (4R,5S)-5-(tert-butyldiphenylsilyloxymethyl)-1-oxa-3-azabicyclo<3.1.0>hexan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-5-(tert-butyldiphenylsilyloxymethyl)-1-oxa-3-azabicyclo<3.1.0>hexan-2-one

There total 3 articles about (4R,5S)-5-(tert-butyldiphenylsilyloxymethyl)-1-oxa-3-azabicyclo<3.1.0>hexan-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: 87.0%

(2S)-1-O-(tert-butyldiphenylsilyl)-2-<(azidocarbonyl)oxy>-3-butene (223763-53-9) → (4R,5S)-5-(tert-butyldiphenylsilyloxymethyl)-1-oxa-3-azabicyclo<3.1.0>hexan-2-one (223763-54-0)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; In dichloromethane; at 109 ℃; for 13h; in ACE Glass Model 8648B pressure tube;

DOI:10.1021/jo9823893

Reference yield:

(S)-1-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-butene (91376-49-7) → (4R,5S)-5-(tert-butyldiphenylsilyloxymethyl)-1-oxa-3-azabicyclo<3.1.0>hexan-2-one (223763-54-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / benzene / 2.5 h / Ambient temperature

2: NaN₃ / dimethylformamide / 19 h / 35 °C

3: 87 percent / BHT / CH₂Cl₂ / 13 h / 109 °C / in ACE Glass Model 8648B pressure tube

With pyridine; sodium azide; 2,6-di-tert-butyl-4-methyl-phenol; In dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo9823893

Reference yield:

carbonic acid 1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl ester 4-nitro-phenyl ester → (4R,5S)-5-(tert-butyldiphenylsilyloxymethyl)-1-oxa-3-azabicyclo<3.1.0>hexan-2-one (223763-54-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NaN₃ / dimethylformamide / 19 h / 35 °C

2: 87 percent / BHT / CH₂Cl₂ / 13 h / 109 °C / in ACE Glass Model 8648B pressure tube

With sodium azide; 2,6-di-tert-butyl-4-methyl-phenol; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo9823893

upstream raw materials:

(2S)-1-O-(tert-butyldiphenylsilyl)-2-<(azidocarbonyl)oxy>-3-butene

(S)-1-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-butene

Downstream raw materials:

5-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-4-(2-methoxy-benzyl)-2-oxo-oxazolidine-3-carboxylic acid tert-butyl ester

(S)-2-{[(4R,5S)-4-(2-Methoxy-benzyl)-2-oxo-oxazolidine-5-carbonyl]-amino}-4-methyl-pentanoic acid tert-butyl ester

(4R,5S)-5-<(2-methoxyphenyl)methyl>-4-(hydroxymethyl)-1,3-oxazolidin-2-one

(4R,5S)-5-<(2-methoxyphenyl)methyl>-4-(tert-butyldiphenylsilyloxymethyl)-1,3-oxazolidin-2-one