6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-ornithinyl(δ-Cbz))-sulfamoyl]adenosine

Base Information

• Chemical Name: 6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-ornithinyl(δ-Cbz))-sulfamoyl]adenosine
• CAS No.: 1356085-27-2
• Molecular Formula: C₄₆H₄₆N₈O₁₃S
• Molecular Weight: 950.983
• Mol file: 1356085-27-2.mol

Synonyms:6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-ornithinyl(δ-Cbz))-sulfamoyl]adenosine

Chemical Property of 6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-ornithinyl(δ-Cbz))-sulfamoyl]adenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-ornithinyl(δ-Cbz))-sulfamoyl]adenosine

There total 7 articles about 6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-ornithinyl(δ-Cbz))-sulfamoyl]adenosine 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: 73.0%

6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-sulfamoyladenosine (1356085-15-8) + (S)-2,5-bis-(benzyloxycarbonylamino)pentanoic acid (2274-58-0) → 6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-ornithinyl(δ-Cbz))-sulfamoyl]adenosine (1356085-27-2)

Guidance literature:

(S)-2,5-bis-(benzyloxycarbonylamino)pentanoic acid; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere;

6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-sulfamoyladenosine; With dmap; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tet.2011.12.011

Reference yield:

2',3'-O,O-benzylidene adenosine (3257-69-0) → 6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-ornithinyl(δ-Cbz))-sulfamoyl]adenosine (1356085-27-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine; 1H-imidazole / 24 h / 20 °C / Inert atmosphere

2.1: dichloromethane / 24 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

3.2: Dowex x 50w

4.1: dmap; sulphamoyl chloride / dichloromethane / 0 - 20 °C / pH 7 / Inert atmosphere

5.1: polystyrene-bound DCC / dichloromethane; N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

5.2: 24 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; sulphamoyl chloride; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2011.12.011

Reference yield:

6-N-benzyloxycarbonyl-2',3'-O-benzylideneadenosine (1356085-12-5) → 6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-ornithinyl(δ-Cbz))-sulfamoyl]adenosine (1356085-27-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; sulphamoyl chloride / dichloromethane / 0 - 20 °C / pH 7 / Inert atmosphere

2.1: polystyrene-bound DCC / dichloromethane; N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

2.2: 24 h / 20 °C / Inert atmosphere

With dmap; sulphamoyl chloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2011.12.011

upstream raw materials:

2',3'-O,O-benzylidene adenosine

6-N-benzyloxycarbonyl-2',3'-O-benzylideneadenosine

6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-sulfamoyladenosine

(S)-2,5-bis-(benzyloxycarbonylamino)pentanoic acid

Downstream raw materials:

5'-Sulfamoyladenosine

5'-O-(N-ornithinylsulfamoyl)adenosine