5'-O-(4,4'-dimethoxytrityl)-3'-O-[P-(β-cyanoethoxy)-N,N-diisopropylaminophosphinyl]-2'-deoxy-2'-C-[(thymin-1-yl)methyl]uridine

Base Information

• Chemical Name: 5'-O-(4,4'-dimethoxytrityl)-3'-O-[P-(β-cyanoethoxy)-N,N-diisopropylaminophosphinyl]-2'-deoxy-2'-C-[(thymin-1-yl)methyl]uridine
• CAS No.: 1392102-74-7
• Molecular Formula: C₄₅H₅₃N₆O₁₀P
• Molecular Weight: 868.924

Synonyms:5'-O-(4,4'-dimethoxytrityl)-3'-O-[P-(β-cyanoethoxy)-N,N-diisopropylaminophosphinyl]-2'-deoxy-2'-C-[(thymin-1-yl)methyl]uridine

Chemical Property of 5'-O-(4,4'-dimethoxytrityl)-3'-O-[P-(β-cyanoethoxy)-N,N-diisopropylaminophosphinyl]-2'-deoxy-2'-C-[(thymin-1-yl)methyl]uridine

Chemical Property:

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Technology Process of 5'-O-(4,4'-dimethoxytrityl)-3'-O-[P-(β-cyanoethoxy)-N,N-diisopropylaminophosphinyl]-2'-deoxy-2'-C-[(thymin-1-yl)methyl]uridine

There total 6 articles about 5'-O-(4,4'-dimethoxytrityl)-3'-O-[P-(β-cyanoethoxy)-N,N-diisopropylaminophosphinyl]-2'-deoxy-2'-C-[(thymin-1-yl)methyl]uridine 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: 83.0%

5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-C-[(thymin-1-yl)methyl]uridine (1392102-73-6) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 5'-O-(4,4'-dimethoxytrityl)-3'-O-[P-(β-cyanoethoxy)-N,N-diisopropylaminophosphinyl]-2'-deoxy-2'-C-[(thymin-1-yl)methyl]uridine (1392102-74-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/chem.201103467

Reference yield:

3-((benzyloxy)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione (119451-90-0) → 5'-O-(4,4'-dimethoxytrityl)-3'-O-[P-(β-cyanoethoxy)-N,N-diisopropylaminophosphinyl]-2'-deoxy-2'-C-[(thymin-1-yl)methyl]uridine (1392102-74-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0.08 h / 100 °C / Inert atmosphere; Microwave irradiation

2.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.75 h / Inert atmosphere; Reflux

2.2: 20 h / 20 °C / Inert atmosphere

3.1: 20 % Pd(OH)2/C; hydrogen / methanol / 17 h / 20 °C

4.1: pyridine / 6 h / 20 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 3 h / 20 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; 20 % Pd(OH)2/C; hydrogen; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; pyridine; methanol; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1002/chem.201103467

Reference yield:

methyl 3,5-di-O-(4-chlorobenzyl)-2-deoxy-2-α-(hydroxymethyl)-α-D-ribofuranoside (733050-13-0) → 5'-O-(4,4'-dimethoxytrityl)-3'-O-[P-(β-cyanoethoxy)-N,N-diisopropylaminophosphinyl]-2'-deoxy-2'-C-[(thymin-1-yl)methyl]uridine (1392102-74-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0.08 h / 100 °C / Inert atmosphere; Microwave irradiation

2.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.75 h / Inert atmosphere; Reflux

2.2: 20 h / 20 °C / Inert atmosphere

3.1: 20 % Pd(OH)2/C; hydrogen / methanol / 17 h / 20 °C

4.1: pyridine / 6 h / 20 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 3 h / 20 °C / Inert atmosphere

With N,O-bis-(trimethylsilyl)-acetamide; 20 % Pd(OH)2/C; hydrogen; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; pyridine; methanol; 1,2-dichloro-ethane; toluene; acetonitrile;

DOI:10.1002/chem.201103467

upstream raw materials:

methyl 2-C-{[N3-(benzyloxymethyl)thymin-1-yl]methyl}-3,5-bis-O-(4-chlorobenzyl)-2-deoxy-α-D-ribofuranoside

2'-C-{[N₃-(benzyloxymethyl)thymin-1-yl]methyl}-3',5'-bis-O-(4-chlorobenzyl)-2'-deoxyuridine

2'-deoxy-2'-C-[(thymin-1-yl)methyl]uridine

4,4'-dimethoxytrityl chloride

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