N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N⁽¹⁾-acetyl)-glycine)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine

Base Information

• Chemical Name: N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N⁽¹⁾-acetyl)-glycine)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine
• CAS No.: 253336-48-0
• Molecular Formula: C₄₅H₄₈Cl₃N₉O₁₁
• Molecular Weight: 997.289

Synonyms:N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N⁽¹⁾-acetyl)-glycine)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine

Chemical Property of N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N⁽¹⁾-acetyl)-glycine)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine

Chemical Property:

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Technology Process of N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N⁽¹⁾-acetyl)-glycine)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine

There total 4 articles about N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N⁽¹⁾-acetyl)-glycine)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine 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: 79.3%

N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N(1)-acetyl)-glycine ethyl ester)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine (287487-40-5) → N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N(1)-acetyl)-glycine)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine (253336-48-0)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 1h; pH=11;

DOI:10.1021/ja000022l

Reference yield:

N-(2-t-butoxycarbonylaminoethyl)-N-(thymin-1-ylacetyl)glycine ethyl ester (149411-93-8) → N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N(1)-acetyl)-glycine)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine (253336-48-0)

Guidance literature:

Multi-step reaction with 4 steps

1: TFA / 0.75 h / 20 °C

2: 68.5 percent / TEA / CH₂Cl₂ / 0.5 h / 0 °C

3: 71 percent / DIPEA; HgCl₂ / dimethylformamide

4: 79.3 percent / aq. NaOH / dioxane / 1 h / pH 11

With sodium hydroxide; TEA; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; mercury dichloride; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1: acidolysis / 2: Addition / 3: Condensation / 4: Hydrolysis;

DOI:10.1021/ja000022l

Reference yield:

N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N(1)-acetyl)-glycine ethyl ester)thiourea (253336-49-1) → N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N(1)-acetyl)-glycine)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine (253336-48-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / DIPEA; HgCl₂ / dimethylformamide

2: 79.3 percent / aq. NaOH / dioxane / 1 h / pH 11

With sodium hydroxide; N-ethyl-N,N-diisopropylamine; mercury dichloride; In 1,4-dioxane; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrolysis;

DOI:10.1021/ja000022l

upstream raw materials:

N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N⁽¹⁾-acetyl)-glycine ethyl ester)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine

N-(2-t-butoxycarbonylaminoethyl)-N-(thymin-1-ylacetyl)glycine ethyl ester

N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N⁽¹⁾-acetyl)-glycine ethyl ester)thiourea

{(2-amino-ethyl)-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid ethyl ester

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