3-N-(9-fluorenylmethoxycarbonyl)amino-4-[(5'-O-4,4'-dimethoxytriphenyl)methyl-2'-deoxy-β-D-ribofuranosyl]biphenyl

Base Information

• Chemical Name: 3-N-(9-fluorenylmethoxycarbonyl)amino-4-[(5'-O-4,4'-dimethoxytriphenyl)methyl-2'-deoxy-β-D-ribofuranosyl]biphenyl
• CAS No.: 936739-67-2
• Molecular Formula: C₅₃H₄₇NO₇
• Molecular Weight: 809.959

Synonyms:3-N-(9-fluorenylmethoxycarbonyl)amino-4-[(5'-O-4,4'-dimethoxytriphenyl)methyl-2'-deoxy-β-D-ribofuranosyl]biphenyl

Chemical Property of 3-N-(9-fluorenylmethoxycarbonyl)amino-4-[(5'-O-4,4'-dimethoxytriphenyl)methyl-2'-deoxy-β-D-ribofuranosyl]biphenyl

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Technology Process of 3-N-(9-fluorenylmethoxycarbonyl)amino-4-[(5'-O-4,4'-dimethoxytriphenyl)methyl-2'-deoxy-β-D-ribofuranosyl]biphenyl

There total 2 articles about 3-N-(9-fluorenylmethoxycarbonyl)amino-4-[(5'-O-4,4'-dimethoxytriphenyl)methyl-2'-deoxy-β-D-ribofuranosyl]biphenyl 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: 74.0%

3-N-(9-fluorenylmethoxycarbonyl)amino-4-(2'-deoxy-β-D-ribofuranosyl)biphenyl (936739-66-1) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 3-N-(9-fluorenylmethoxycarbonyl)amino-4-[(5'-O-4,4'-dimethoxytriphenyl)methyl-2'-deoxy-β-D-ribofuranosyl]biphenyl (936739-67-2)

Guidance literature:

With pyridine; for 3.5h;

DOI:10.1016/j.tet.2006.12.095

Reference yield:

3-N-(9-fluorenylmethoxycarbonyl)amino-4-(2'-deoxy-3',5'-O-tetraisopropyl-oxydisilyl-D-ribofuranosyl)biphenyl → 3-N-(9-fluorenylmethoxycarbonyl)amino-4-[(5'-O-4,4'-dimethoxytriphenyl)methyl-2'-deoxy-β-D-ribofuranosyl]biphenyl (936739-67-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / (HF)3*NEt₃ / tetrahydrofuran / 14 h / 20 °C

2: 74 percent / pyridine / 3.5 h

With pyridine; triethylamine tris(hydrogen fluoride); In tetrahydrofuran;

DOI:10.1016/j.tet.2006.12.095

Reference yield: 81.0%

3-N-(9-fluorenylmethoxycarbonyl)amino-4-[(5'-O-4,4'-dimethoxytriphenyl)methyl-2'-deoxy-β-D-ribofuranosyl]biphenyl (936739-67-2) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 3-N-(9-fluorenylmethoxycarbonyl)amino-4-[(5'-O-4,4'-dimethoxytriphenyl)methyl-3'-(N,N-diisopropylamino-2-cyanoethyl-phosphino)-2'-deoxy-β-D-ribofuranosyl]biphenyl

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1016/j.tet.2006.12.095

upstream raw materials:

3-N-(9-fluorenylmethoxycarbonyl)amino-4-(2'-deoxy-β-D-ribofuranosyl)biphenyl

4,4'-dimethoxytrityl chloride

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