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

Base Information

• Chemical Name: N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N⁽¹⁾-acetyl)-glycine ethyl ester)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine
• CAS No.: 287487-40-5
• Molecular Formula: C₄₇H₅₂Cl₃N₉O₁₁
• Molecular Weight: 1025.34

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

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

There total 3 articles about N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N⁽¹⁾-acetyl)-glycine ethyl ester)-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: 71.0%

5'-monomethoxytritylamino-3'-amino-2',3',5'-trideoxythymidine (209255-51-6) + 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 ethyl ester)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine (287487-40-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; mercury dichloride; In N,N-dimethyl-formamide;

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 ethyl ester)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine (287487-40-5)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/ja000022l

Reference yield:

{(2-amino-ethyl)-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid ethyl ester (169452-45-3) → N-trichloroethoxycarbonyl-N'-((aminoethyl)-N-(thyminyl-N(1)-acetyl)-glycine ethyl ester)-N''-(5'-N-monomethoxytrityl-3',5'-dideoxythymidine)guanidine (287487-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 68.5 percent / TEA / CH₂Cl₂ / 0.5 h / 0 °C

2: 71 percent / DIPEA; HgCl₂ / dimethylformamide

With TEA; N-ethyl-N,N-diisopropylamine; mercury dichloride; In dichloromethane; N,N-dimethyl-formamide; 1: Addition / 2: Condensation;

DOI:10.1021/ja000022l

upstream raw materials:

5'-monomethoxytritylamino-3'-amino-2',3',5'-trideoxythymidine

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

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

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

Downstream raw materials:

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

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