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

Base Information

Chemical Name:6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-valinyl)sulfamoyl]adenosine
CAS No.:1356085-18-1
Molecular Formula:C₃₈H₃₉N₇O₁₁S
Molecular Weight:801.834
Hs Code.:

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

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

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

There total 7 articles about 6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-valinyl)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: 85.0%

: 1149-26-4
(S)-N-(benzyloxycarbonyl)valine

: 1356085-15-8
6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-sulfamoyladenosine

: 1356085-18-1
6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-valinyl)sulfamoyl]adenosine

Guidance literature:: (S)-N-(benzyloxycarbonyl)valine; 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:

: 1356085-12-5
6-N-benzyloxycarbonyl-2',3'-O-benzylideneadenosine

: 1356085-18-1
6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-valinyl)sulfamoyl]adenosine

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

Reference yield:

: 1356085-05-6
2',3'-O-benzylidene-5'-O-(tert-butyldimethylsilyl)adenosine

: 1356085-18-1
6-N-benzyloxycarbonyl-2',3'-O-benzylidene-5'-O-[N-(N-Cbz-L-valinyl)sulfamoyl]adenosine

Guidance literature:: Multi-step reaction with 4 steps

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

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

2.2: Dowex x 50w

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

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

4.2: 24 h / 20 °C / Inert atmosphere

With dmap; sulphamoyl chloride; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2011.12.011