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

Base Information

• Chemical Name: benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate
• CAS No.: 796869-90-4
• Molecular Formula: C₃₆H₄₈N₂O₁₀SSi
• Molecular Weight: 728.936
• Mol file: 796869-90-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate 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: 88.0%

t-butyldimethylsiyl triflate (69739-34-0) + benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-hydroxy-6-methylsulfonyloxyhexanoate (796869-99-3) → benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate (796869-90-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2004.09.033

Reference yield:

benzyl (2S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5,6-dihydroxyhexanoate → benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate (796869-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CHCl₃ / 6 h / 20 °C

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

With pyridine; 2,6-dimethylpyridine; In dichloromethane; chloroform;

DOI:10.1055/s-2007-983785

Reference yield:

O-benzylhydoxylamine hydrochloride (2687-43-6) → benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-tert-butyldimethylsilyloxy-6-methylsulfonyloxyhexanoate (796869-90-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / NaHCO₃; HOBt; EDCI / 12 h / 0 - 20 °C

2: 86 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

3: 91 percent / Et₃N / CHCl₃ / 12 h / 20 °C

4: 88 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 20 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; chloroform;

DOI:10.1016/j.tetlet.2004.09.033

upstream raw materials:

t-butyldimethylsiyl triflate

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

O-benzylhydoxylamine hydrochloride

benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5,6-dihydroxyhexanoate

Downstream raw materials:

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

(3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonyl-3'-benzyloxycarbonylaminopropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone

(3R,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonyl-3'-benzyloxycarbonylaminopropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone

(3R,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonyl-3'-benzyloxycarbonylaminopropyl)-3-hydroxy-2-azetidinone