(R)-2-<(R)-2-tert-butyldiphenylsilyloxy-1-(N-tosylamino)ethyl>oxirane

Base Information

• Chemical Name: (R)-2-<(R)-2-tert-butyldiphenylsilyloxy-1-(N-tosylamino)ethyl>oxirane
• CAS No.: 152897-54-6
• Molecular Formula: C₂₇H₃₃NO₄SSi
• Molecular Weight: 495.715
• Mol file: 152897-54-6.mol

Synonyms:(R)-2-<(R)-2-tert-butyldiphenylsilyloxy-1-(N-tosylamino)ethyl>oxirane

Chemical Property of (R)-2-<(R)-2-tert-butyldiphenylsilyloxy-1-(N-tosylamino)ethyl>oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-<(R)-2-tert-butyldiphenylsilyloxy-1-(N-tosylamino)ethyl>oxirane

There total 8 articles about (R)-2-<(R)-2-tert-butyldiphenylsilyloxy-1-(N-tosylamino)ethyl>oxirane 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: 95.0%

(2R,3S)-2-tert-butyldiphenylsilyloxymethyl-3-hydroxymethyl-N-tosylaziridine (152897-49-9) → (R)-2-<(R)-2-tert-butyldiphenylsilyloxy-1-(N-tosylamino)ethyl>oxirane (152897-54-6)

Guidance literature:

With lithium tert-butoxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/S0040-4039(00)60694-9

Reference yield:

Acetic acid (2R,3S)-3-hydroxymethyl-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl ester (132835-12-2) → (R)-2-<(R)-2-tert-butyldiphenylsilyloxy-1-(N-tosylamino)ethyl>oxirane (152897-54-6)

Guidance literature:

Multi-step reaction with 5 steps

1: p-toluenesulfinic acid / CH₂Cl₂ / Ambient temperature

2: 99 percent / K₂CO₃ / methanol / 0.25 h / 0 °C

3: 99 percent / triethylamine, 4-dimethylaminopyridine / dimethylformamide / Ambient temperature

4: 95 percent / 0.5 M aq. HCl / tetrahydrofuran / 15 h / 0 °C

5: 95 percent / t-BuOLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 deg C, 1 h, 0 deg C, 2 h

With hydrogenchloride; dmap; p-toluene sulfinic acid; potassium carbonate; triethylamine; lithium tert-butoxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.3987/COM-95-S76

Reference yield:

[(2R,3S)-3-(2-Ethoxy-ethoxymethyl)-1-(toluene-4-sulfonyl)-aziridin-2-yl]-methanol (174096-53-8) → (R)-2-<(R)-2-tert-butyldiphenylsilyloxy-1-(N-tosylamino)ethyl>oxirane (152897-54-6)

Guidance literature:

Multi-step reaction with 3 steps

1: NEt₃, DMAP

2: 0.5 M HCl / tetrahydrofuran

3: 95 percent / t-BuOLi / hexamethylphosphoric acid triamide; tetrahydrofuran

With hydrogenchloride; dmap; triethylamine; lithium tert-butoxide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/S0040-4039(00)60694-9

upstream raw materials:

(2R,3S)-2-tert-butyldiphenylsilyloxymethyl-3-hydroxymethyl-N-tosylaziridine

Acetic acid (2R,3S)-3-hydroxymethyl-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl ester

[(2R,3S)-3-(2-Ethoxy-ethoxymethyl)-1-(toluene-4-sulfonyl)-aziridin-2-yl]-methanol

Acetic acid (2R,3S)-3-(2-ethoxy-ethoxymethyl)-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl ester

Downstream raw materials:

(3S,4S)-5-tert-butyldiphenylsilyloxy-3-hydroxy-4-(N-tosylamino)pentanenitrile

(3S,4S)-3,5-dihydroxy-4-(N-tosylamino)pentanenitrile

(3S,4R)-3-hydroxy-5-iodo-4-(N-tosylamino)pentanenitrile

(3S,4S)-3-hydroxy-5-phenyl-4-(N-tosylamino)pentanenitrile