N⁴-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-2'-deoxycytidine

Base Information

• Chemical Name: N⁴-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-2'-deoxycytidine
• CAS No.: 776297-87-1
• Molecular Formula: C₃₁H₅₀N₆O₁₁
• Molecular Weight: 682.772

Synonyms:N⁴-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-2'-deoxycytidine

Chemical Property of N⁴-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-2'-deoxycytidine

Chemical Property:

Purity/Quality:

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Technology Process of N⁴-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-2'-deoxycytidine

There total 9 articles about N⁴-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-2'-deoxycytidine 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%

N4-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxycytidine (776297-86-0) → N4-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-2'-deoxycytidine (776297-87-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 18 ℃; for 18h;

DOI:10.1055/s-2004-829143

Reference yield:

{[2-(bis-ethoxycarbonylmethyl-amino)-ethyl]-ethoxycarbonylmethyl-amino}-acetic acid (90359-20-9) → N4-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-2'-deoxycytidine (776297-87-1)

Guidance literature:

Multi-step reaction with 5 steps

1: N-methylmorpholine / tetrahydrofuran / 0.33 h / -15 °C

2: 870 mg / tetrahydrofuran / 18 h / 4 °C

3: 81 percent / TFA / CH₂Cl₂ / 0.5 h / 18 °C

4: 75 percent / ethanol / 1 h / 60 °C

5: 83 percent / TBAF / tetrahydrofuran / 18 h / 18 °C

With 4-methyl-morpholine; tetrabutyl ammonium fluoride; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1055/s-2004-829143

Reference yield:

[[2-(bis-ethoxycarbonylmethyl-amino)-ethyl]-(2-isobutoxycarbonyloxy-2-oxo-ethyl)-amino]-acetic acid ethyl ester → N4-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-2'-deoxycytidine (776297-87-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 870 mg / tetrahydrofuran / 18 h / 4 °C

2: 81 percent / TFA / CH₂Cl₂ / 0.5 h / 18 °C

3: 75 percent / ethanol / 1 h / 60 °C

4: 83 percent / TBAF / tetrahydrofuran / 18 h / 18 °C

With tetrabutyl ammonium fluoride; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1055/s-2004-829143

upstream raw materials:

N⁴-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxycytidine

trans-1,4-cyclohexyldiamine

{[2-(bis-ethoxycarbonylmethyl-amino)-ethyl]-ethoxycarbonylmethyl-amino}-acetic acid

trans-N-Boc-1,4-cyclohexanediamine

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-N⁴-[trans-4-(2-{[2-bis(ethoxycarbonylmethylamino)ethyl]ethoxycarbonylmethylamino}acetylamino)cyclohexyl]-2'-deoxycytidine

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