1-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]-5-methyl-2-pyrimidinone

Base Information

• Chemical Name: 1-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]-5-methyl-2-pyrimidinone
• CAS No.: 599178-14-0
• Molecular Formula: C₃₅H₃₆F₃N₃O₈
• Molecular Weight: 683.681
• Mol file: 599178-14-0.mol

Synonyms:1-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]-5-methyl-2-pyrimidinone

Chemical Property of 1-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]-5-methyl-2-pyrimidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]-5-methyl-2-pyrimidinone

There total 12 articles about 1-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]-5-methyl-2-pyrimidinone 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) + 5-methyl-1-[2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]-2-pyrimidinone (599178-10-6) → 1-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]-5-methyl-2-pyrimidinone (599178-14-0)

Guidance literature:

With pyridine; at 20 ℃; for 6.5h;

DOI:10.1002/ejoc.200600182

Reference yield:

(6aR,8R,9R,9aS)-2,2,4,4-tetraisopropyl-8-methoxytetrahydro-6H-furo[3,2- f][1,3,5,2,4]trioxadisilocin-9-ol (76700-76-0) → 1-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]-5-methyl-2-pyrimidinone (599178-14-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 77 percent / sodium hydride / dimethylformamide / 10 h / -10 - 20 °C

2: 94 percent / LiBH₄ / tetrahydrofuran; methanol / 1 h / 0 °C

3: 93 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

4: 96 percent / LiN₃ / dimethylformamide / 1.5 h / 90 °C

5: 100 percent / hydrogen / Lindlar catalyst / tetrahydrofuran / 20 °C

6: 89 percent / triethylamine / 4 h / 20 °C

7: 91 percent / acetic acid; H₂SO₄ / 14 h / 20 °C

8: 55 percent / N,O-bis(trimethylsilyl) acetamide; SnCl₄ / acetonitrile / 2 h / 0 °C

9: 90 percent / Na₂CO₃ / methanol / 0.5 h / 20 °C

10: 75 percent / pyridine / 5 h / 20 °C

With pyridine; dmap; lithium borohydride; N,O-bis-(trimethylsilyl)-acetamide; lithium azide; sulfuric acid; hydrogen; tin(IV) chloride; sodium hydride; sodium carbonate; acetic acid; triethylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1081/NCN-120022835

Reference yield:

1-O-methyl-D-ribofuranose (7473-45-2) → 1-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]-5-methyl-2-pyrimidinone (599178-14-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 83 percent / pyridine / 1 h / 20 °C

2: 77 percent / sodium hydride / dimethylformamide / 10 h / -10 - 20 °C

3: 94 percent / LiBH₄ / tetrahydrofuran; methanol / 1 h / 0 °C

4: 93 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

5: 96 percent / LiN₃ / dimethylformamide / 1.5 h / 90 °C

6: 100 percent / hydrogen / Lindlar catalyst / tetrahydrofuran / 20 °C

7: 89 percent / triethylamine / 4 h / 20 °C

8: 91 percent / acetic acid; H₂SO₄ / 14 h / 20 °C

9: 55 percent / N,O-bis(trimethylsilyl) acetamide; SnCl₄ / acetonitrile / 2 h / 0 °C

10: 90 percent / Na₂CO₃ / methanol / 0.5 h / 20 °C

11: 75 percent / pyridine / 5 h / 20 °C

With pyridine; dmap; lithium borohydride; N,O-bis-(trimethylsilyl)-acetamide; lithium azide; sulfuric acid; hydrogen; tin(IV) chloride; sodium hydride; sodium carbonate; acetic acid; triethylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1081/NCN-120022835

upstream raw materials:

4,4'-dimethoxytrityl chloride

5-methyl-1-[2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]-2-pyrimidinone

5-methyl-pyrimidin-2-(1H)-one

1,3,5-tri-O-acetyl-2-O-(2-trifluoroacetamido)ethyl-D-ribofuranoside