N-[N₁-(8-tert-butoxycarbonylamino-3,6-dioxaoct-1-yl)-1,2,3-triazol-4-yl]methyl-N-[N₆-(benzyloxycarbonyl)adenin-9-ylacetyl]glycineethyl ester

Base Information

• Chemical Name: N-[N₁-(8-tert-butoxycarbonylamino-3,6-dioxaoct-1-yl)-1,2,3-triazol-4-yl]methyl-N-[N₆-(benzyloxycarbonyl)adenin-9-ylacetyl]glycineethyl ester
• CAS No.: 1349193-24-3
• Molecular Formula: C₃₃H₄₄N₁₀O₉
• Molecular Weight: 724.774

Synonyms:N-[N₁-(8-tert-butoxycarbonylamino-3,6-dioxaoct-1-yl)-1,2,3-triazol-4-yl]methyl-N-[N₆-(benzyloxycarbonyl)adenin-9-ylacetyl]glycineethyl ester

Chemical Property of N-[N₁-(8-tert-butoxycarbonylamino-3,6-dioxaoct-1-yl)-1,2,3-triazol-4-yl]methyl-N-[N₆-(benzyloxycarbonyl)adenin-9-ylacetyl]glycineethyl ester

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Technology Process of N-[N₁-(8-tert-butoxycarbonylamino-3,6-dioxaoct-1-yl)-1,2,3-triazol-4-yl]methyl-N-[N₆-(benzyloxycarbonyl)adenin-9-ylacetyl]glycineethyl ester

There total 8 articles about N-[N₁-(8-tert-butoxycarbonylamino-3,6-dioxaoct-1-yl)-1,2,3-triazol-4-yl]methyl-N-[N₆-(benzyloxycarbonyl)adenin-9-ylacetyl]glycineethyl ester 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: 64.0%

{2-[2-(2-azidoethoxy)ethoxy]ethyl}carbamic acid tert-butyl ester (950683-55-3) + N-[N6-(benzyloxycarbonyl)adenin-9-ylacetyl]-N-(propyn-3-yl)glycine ethyl ester (1349193-21-0) → N-[N1-(8-tert-butoxycarbonylamino-3,6-dioxaoct-1-yl)-1,2,3-triazol-4-yl]methyl-N-[N6-(benzyloxycarbonyl)adenin-9-ylacetyl]glycineethyl ester (1349193-24-3)

Guidance literature:

With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In dichloromethane; water; tert-butyl alcohol; at 20 ℃; for 48h;

DOI:10.1016/j.tet.2011.09.124

Reference yield:

2-(2-(2-aminoethoxy)ethoxy)ethan-1-ol (6338-55-2) → N-[N1-(8-tert-butoxycarbonylamino-3,6-dioxaoct-1-yl)-1,2,3-triazol-4-yl]methyl-N-[N6-(benzyloxycarbonyl)adenin-9-ylacetyl]glycineethyl ester (1349193-24-3)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / methanol / 3 h / Reflux

2: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 4 h / 60 °C / Inert atmosphere

4: copper(ll) sulfate pentahydrate; sodium L-ascorbate / dichloromethane; water; tert-butyl alcohol / 48 h / 20 °C

With sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate; triethylamine; In methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/j.tet.2011.09.124

Reference yield:

tert-butyl 2-(2-(2-hydroxyethoxy)ethoxy)ethylcarbamate (139115-92-7) → N-[N1-(8-tert-butoxycarbonylamino-3,6-dioxaoct-1-yl)-1,2,3-triazol-4-yl]methyl-N-[N6-(benzyloxycarbonyl)adenin-9-ylacetyl]glycineethyl ester (1349193-24-3)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2: sodium azide / N,N-dimethyl-formamide / 4 h / 60 °C / Inert atmosphere

3: copper(ll) sulfate pentahydrate; sodium L-ascorbate / dichloromethane; water; tert-butyl alcohol / 48 h / 20 °C

With sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate; triethylamine; In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/j.tet.2011.09.124

upstream raw materials:

2,2-dimethyl-4-oxo-3,8,11-trioxa-5-azatridecane-13-yl methanesulfonate

{2-[2-(2-azidoethoxy)ethoxy]ethyl}carbamic acid tert-butyl ester

N-[N₆-(benzyloxycarbonyl)adenin-9-ylacetyl]-N-(propyn-3-yl)glycine ethyl ester

8-dibenzylamino-3,6-dioxaoctanoic acid ethyl ester

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