(3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonylamino-3'-carboxypropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone

Base Information

• Chemical Name: (3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonylamino-3'-carboxypropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone
• CAS No.: 796869-92-6
• Molecular Formula: C₂₈H₃₈N₂O₇Si
• Molecular Weight: 542.704
• Mol file: 796869-92-6.mol

Synonyms:(3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonylamino-3'-carboxypropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone

Chemical Property of (3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonylamino-3'-carboxypropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonylamino-3'-carboxypropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone

There total 9 articles about (3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonylamino-3'-carboxypropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone 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: 59.0%

benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate (796869-90-4) → (3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonylamino-3'-carboxypropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone (796869-92-6) + (3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonyl-3'-benzyloxycarbonylaminopropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone (796869-91-5)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; at -78 - 0 ℃; for 24h;

DOI:10.1016/j.tetlet.2004.09.033

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonylamino-3'-carboxypropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone (796869-92-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

2: 11 percent / KHMDS / tetrahydrofuran; toluene / 12 h / -78 - 0 °C

With 2,6-dimethylpyridine; potassium hexamethylsilazane; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1055/s-2007-983785

Reference yield:

benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-hydroxy-6-methylsulfonyloxyhexanoate (796869-99-3) → (3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonylamino-3'-carboxypropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone (796869-92-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

2: 11 percent / KHMDS / tetrahydrofuran; toluene / 12 h / -78 - 0 °C

With 2,6-dimethylpyridine; potassium hexamethylsilazane; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1055/s-2007-983785

upstream raw materials:

benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate

t-butyldimethylsiyl triflate

benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-hydroxy-6-methylsulfonyloxyhexanoate

O-benzylhydoxylamine hydrochloride

Downstream raw materials:

(3S,3'S)-3-(3'-amino-3'-carboxypropyl)-3-hydroxy-2-azetidinone