6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-glycyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine

Base Information

• Chemical Name: 6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-glycyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine
• CAS No.: 1333992-29-2
• Molecular Formula: C₅₇H₆₂N₈O₈
• Molecular Weight: 987.168

Synonyms:6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-glycyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine

Chemical Property of 6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-glycyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-glycyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine

There total 2 articles about 6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-glycyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-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:

3'-azido-6-N-[(di-n-butylamino)methylene]-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine (1173243-10-1) + Fmoc-Gly-OBt (117830-89-4) → 6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-glycyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine (1333992-29-2)

Guidance literature:

With trimethylphosphane; In tetrahydrofuran; at 0 - 20 ℃; for 16.25h;

DOI:10.1016/j.bmc.2011.07.018

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) → 6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-glycyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine (1333992-29-2)

Guidance literature:

Multi-step reaction with 2 steps

1: diisopropyl-carbodiimide / tetrahydrofuran / 0.33 h / 0 °C

2: trimethylphosphane / tetrahydrofuran / 16.25 h / 0 - 20 °C

With diisopropyl-carbodiimide; trimethylphosphane; In tetrahydrofuran;

DOI:10.1016/j.bmc.2011.07.018

Reference yield: 67.0%

6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-glycyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine (1333992-29-2) + Hexane-1,6-dioic acid bis(pentafluorophenyl) ester (83701-40-0) → 6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-glycyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-O-[1,6-dioxo-6-(pentafluorophenyloxy)hexyl]-β-D-adenosine (1333992-34-9)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 2h;

DOI:10.1016/j.bmc.2011.07.018

upstream raw materials:

3'-azido-6-N-[(di-n-butylamino)methylene]-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine

Fmoc-Gly-OBt

N-(fluoren-9-ylmethoxycarbonyl)glycine

Downstream raw materials:

6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-glycyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-O-[1,6-dioxo-6-(pentafluorophenyloxy)hexyl]-β-D-adenosine

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