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

Base Information

• Chemical Name: methyl 5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate
• CAS No.: 289712-90-9
• Molecular Formula: C₃₄H₃₆N₂O₉
• Molecular Weight: 616.668
• Mol file: 289712-90-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about methyl 5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate 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: 84.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + methyl 5-(2'-deoxy-β-D-erythro-pentofuranosyl)-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate (289712-89-6) → 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)

Guidance literature:

With pyridine; at 20 ℃; for 4h;

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

Reference yield:

2'-Deoxypseudouridine (39967-60-7) → 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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; triethylamine carbonate; In ethanol; 1: Michael addition / 2: Alkylation;

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

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

upstream raw materials:

4,4'-dimethoxytrityl chloride

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

2'-Deoxypseudouridine

Downstream raw materials:

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

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