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

Base Information

• Chemical Name: (2S)-1-O-(tert-butyldiphenylsilyl)-2-<(azidocarbonyl)oxy>-3-butene
• CAS No.: 223763-53-9
• Molecular Formula: C₂₁H₂₅N₃O₃Si
• Molecular Weight: 395.533
• Mol file: 223763-53-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (2S)-1-O-(tert-butyldiphenylsilyl)-2-<(azidocarbonyl)oxy>-3-butene 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:

carbonic acid 1-(tert-butyl-diphenyl-silanyloxymethyl)-allyl ester 4-nitro-phenyl ester → (2S)-1-O-(tert-butyldiphenylsilyl)-2-<(azidocarbonyl)oxy>-3-butene (223763-53-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 35 ℃; for 19h; Yield given;

DOI:10.1021/jo9823893

Reference yield:

(S)-1-(tert-butyldiphenylsilyloxy)-2-hydroxy-3-butene (91376-49-7) → (2S)-1-O-(tert-butyldiphenylsilyl)-2-<(azidocarbonyl)oxy>-3-butene (223763-53-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / benzene / 2.5 h / Ambient temperature

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

With pyridine; sodium azide; In N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo9823893

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

upstream raw materials:

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

Downstream raw materials:

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

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

(4R,5S)-5-pentyl-4-(tert-butyldiphenylsilyloxymethyl)-1,3-oxazolidin-2-one

(4R,5S)-5-benzyl-4-(tert-butyldiphenylsilyloxymethyl)-1,3-oxazolidin-2-one