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

Base Information

• Chemical Name: (3S,4S)-5-tert-butyldiphenylsilyloxy-3-hydroxy-4-(N-tosylamino)pentanenitrile
• CAS No.: 152897-55-7
• Molecular Formula: C₂₈H₃₄N₂O₄SSi
• Molecular Weight: 522.74
• Mol file: 152897-55-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (3S,4S)-5-tert-butyldiphenylsilyloxy-3-hydroxy-4-(N-tosylamino)pentanenitrile 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%

potassium cyanide (151-50-8) + (R)-2-<(R)-2-tert-butyldiphenylsilyloxy-1-(N-tosylamino)ethyl>oxirane (152897-54-6) → (3S,4S)-5-tert-butyldiphenylsilyloxy-3-hydroxy-4-(N-tosylamino)pentanenitrile (152897-55-7)

Guidance literature:

With lithium perchlorate; In acetonitrile;

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) → (3S,4S)-5-tert-butyldiphenylsilyloxy-3-hydroxy-4-(N-tosylamino)pentanenitrile (152897-55-7)

Guidance literature:

Multi-step reaction with 6 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

6: 95 percent / LiClO₄ / acetonitrile / Ambient temperature

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

DOI:10.3987/COM-95-S76

Reference yield:

(2R,3S)-2-tert-butyldiphenylsilyloxymethyl-3-hydroxymethyl-N-tosylaziridine (152897-49-9) → (3S,4S)-5-tert-butyldiphenylsilyloxy-3-hydroxy-4-(N-tosylamino)pentanenitrile (152897-55-7)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 95 percent / LiClO₄ / acetonitrile / Ambient temperature

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

DOI:10.3987/COM-95-S76

upstream raw materials:

potassium cyanide

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

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

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

Downstream raw materials:

(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

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