N¹-(3-aminopropyl)-5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanamide

Base Information

• Chemical Name: N¹-(3-aminopropyl)-5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanamide
• CAS No.: 289712-92-1
• Molecular Formula: C₃₆H₄₂N₄O₈
• Molecular Weight: 658.751

Synonyms:N¹-(3-aminopropyl)-5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanamide

Chemical Property of N¹-(3-aminopropyl)-5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanamide

Chemical Property:

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Safty Information:

• Pictogram(s):  
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Technology Process of N¹-(3-aminopropyl)-5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanamide

There total 4 articles about N¹-(3-aminopropyl)-5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanamide 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: 89.0%

Trimethylenediamine (109-76-2,54018-94-9) + methyl 5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate (289712-90-9) → N1-(3-aminopropyl)-5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanamide (289712-92-1)

Guidance literature:

In isopropyl alcohol; at 20 ℃; for 49h;

DOI:10.1002/1522-2675(20000607)83:6<1108::AID-HLCA1108>3.0.CO;2-9

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → N1-(3-aminopropyl)-5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanamide (289712-92-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / pyridine / 4 h / 20 °C

2: 89 percent / propan-2-ol / 49 h / 20 °C

With pyridine; In isopropyl alcohol; 1: Alkylation / 2: amidation;

DOI:10.1002/1522-2675(20000607)83:6<1108::AID-HLCA1108>3.0.CO;2-9

Reference yield:

2'-Deoxypseudouridine (39967-60-7) → N1-(3-aminopropyl)-5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanamide (289712-92-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / (Et₃NH)HCO₃ / ethanol / 20 h / 20 °C / pH 8.5

2: 84 percent / pyridine / 4 h / 20 °C

3: 89 percent / propan-2-ol / 49 h / 20 °C

With pyridine; triethylamine carbonate; In ethanol; isopropyl alcohol; 1: Michael addition / 2: Alkylation / 3: amidation;

DOI:10.1002/1522-2675(20000607)83:6<1108::AID-HLCA1108>3.0.CO;2-9

upstream raw materials:

Trimethylenediamine

methyl 5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate

4,4'-dimethoxytrityl chloride

2'-Deoxypseudouridine

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