[(2R,3R,3aR,9aR)-2-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-acetic acid methyl ester

Base Information

• Chemical Name: [(2R,3R,3aR,9aR)-2-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-acetic acid methyl ester
• CAS No.: 200423-85-4
• Molecular Formula: C₃₃H₅₂N₂O₁₀Si₂
• Molecular Weight: 692.954
• Mol file: 200423-85-4.mol

Synonyms:[(2R,3R,3aR,9aR)-2-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-acetic acid methyl ester

Chemical Property of [(2R,3R,3aR,9aR)-2-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3R,3aR,9aR)-2-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-acetic acid methyl ester

There total 1 articles about [(2R,3R,3aR,9aR)-2-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-acetic acid methyl 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: 98.0%

bromoacetic acid methyl ester (96-32-2) + 3-Benzyloxymethyl-1-((2R,3R,3aS,9aR)-3-hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-5-methyl-1H-pyrimidine-2,4-dione → [(2R,3R,3aR,9aR)-2-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-acetic acid methyl ester (200423-85-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -5 ℃; for 1.5h;

DOI:10.1002/(SICI)1521-3773(19980518)37:9<1288::AID-ANIE1288>3.0.CO;2-U

Reference yield: 84.0%

[(2R,3R,3aR,9aR)-2-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-acetic acid methyl ester (200423-85-4) → 2'-O-(2-hydroxyethyl)-3',5'-O-tetraisopropyl-di-siloxyl-N3-benzyloxymethyl-5-methyl uridine (200423-86-5)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; methanol; at 5 ℃; for 1.5h;

DOI:10.1002/(SICI)1521-3773(19980518)37:9<1288::AID-ANIE1288>3.0.CO;2-U

Reference yield:

[(2R,3R,3aR,9aR)-2-(3-Benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-acetic acid methyl ester (200423-85-4) → N-[2-((2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-2-{5-methyl-4-[1-methyl-pyrrolidin-(2Z)-ylideneamino]-2-oxo-2H-pyrimidin-1-yl}-tetrahydro-furan-3-yloxy)-ethyl]-2,2,2-trifluoro-acetamide

Guidance literature:

Multi-step reaction with 10 steps

1: 84 percent / LiBH₄ / methanol; tetrahydrofuran / 1.5 h / 5 °C

2: 89 percent / NEt₃, DMAP / CH₂Cl₂ / 8 h / 22 °C

3: 88 percent / H₂, HCl / Pd/C / tetrahydrofuran; methanol / 7 h / 22 °C

4: 92 percent / NaN₃ / dimethylformamide / 3 h / 65 °C

5: 1.) triazole, POCl₃, NEt₃, 2.) NH₄OH / 1.) CH₃CN, CH₂Cl₂, 22 deg C, 3 h, 2.) dioxane, 22 deg C, 1 h

6: 95 percent / pyridine / 3 h / 22 °C

7: H₂ / Pd/C / methanol; tetrahydrofuran / 3 h / 22 °C

8: NEt₃ / methanol / 1 h / 22 °C

9: 100 percent / TBAF / tetrahydrofuran / 1 h / 22 °C

10: 85 percent / pyridine / 1 h / 22 °C

With pyridine; 1,2,3-triazole; hydrogenchloride; dmap; ammonium hydroxide; lithium borohydride; sodium azide; tetrabutyl ammonium fluoride; hydrogen; triethylamine; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1521-3773(19980518)37:9<1288::AID-ANIE1288>3.0.CO;2-U

upstream raw materials:

bromoacetic acid methyl ester

Downstream raw materials:

2'-O-(2-hydroxyethyl)-3',5'-O-tetraisopropyl-di-siloxyl-N³-benzyloxymethyl-5-methyl uridine

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

Toluene-4-sulfonic acid 2-[(2R,3R,3aR,9aR)-2-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethyl ester