(S)-2',3'-O-(2-bromo-1-diethylphosphonoethylidene)-5'-O-tert-butyldiphenylsilyl-5-methyluridine

Base Information

• Chemical Name: (S)-2',3'-O-(2-bromo-1-diethylphosphonoethylidene)-5'-O-tert-butyldiphenylsilyl-5-methyluridine
• CAS No.: 214039-19-7
• Molecular Formula: C₃₂H₄₂BrN₂O₉PSi
• Molecular Weight: 737.657

Synonyms:(S)-2',3'-O-(2-bromo-1-diethylphosphonoethylidene)-5'-O-tert-butyldiphenylsilyl-5-methyluridine

Chemical Property of (S)-2',3'-O-(2-bromo-1-diethylphosphonoethylidene)-5'-O-tert-butyldiphenylsilyl-5-methyluridine

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Technology Process of (S)-2',3'-O-(2-bromo-1-diethylphosphonoethylidene)-5'-O-tert-butyldiphenylsilyl-5-methyluridine

There total 1 articles about (S)-2',3'-O-(2-bromo-1-diethylphosphonoethylidene)-5'-O-tert-butyldiphenylsilyl-5-methyluridine 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: 52.0%

diethyl phosphorylchloridite (589-57-1) + 2',3'-O-(2-bromo-1-ethoxyethylidene)-5'-O-tertbutyldiphenylsilyl-5-methyluridine → (S)-2',3'-O-(2-bromo-1-diethylphosphonoethylidene)-5'-O-tert-butyldiphenylsilyl-5-methyluridine (214039-19-7)

Guidance literature:

In acetonitrile; at -40 - 20 ℃;

DOI:10.1016/S0040-4020(98)00653-X

Reference yield: 64.0%

(S)-2',3'-O-(2-bromo-1-diethylphosphonoethylidene)-5'-O-tert-butyldiphenylsilyl-5-methyluridine (214039-19-7) → 2,2'-anhydro-5'-O-tert-butyldiphenylsilyl-3'-O-ethylphosphonoacetyl-5-methyluridine + (ethoxy-hydroxy-phosphoryl)-acetic acid 5-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester + (ethoxy-hydroxy-phosphoryl)-acetic acid 2-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 130 ℃; for 1h;

DOI:10.1016/S0040-4020(98)00653-X

Reference yield: 56.0%

(S)-2',3'-O-(2-bromo-1-diethylphosphonoethylidene)-5'-O-tert-butyldiphenylsilyl-5-methyluridine (214039-19-7) → 3'-O-acetyl-5'-O-tert-butyldiphenylsilyl-5-methyluridine + 2'-O-acetyl-5'-O-tert-butyldiphenylsilyl-5-methyluridine + (S)-2',3'-O-(2-bromo-1-ethylphosphonoethylidene)-5'-O-tert-butyldiphenylsilyl-5-methyluridine

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(98)00653-X

upstream raw materials:

diethyl phosphorylchloridite

Downstream raw materials:

5-Methyluridine

5′-O-tert-butyldiphenylsilyl-O²-2′-anhydro-5-methyluridine

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