1-[(1R,2R,3aR,9aS)-5'-oxo-6,6,8,8-tetrakis(propan-2-yl)-hexahydrospiro[furo[3,2-f][1,3,5,2,4]trioxadisilocine-1,2-pyrrolidine]-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl 2,4,6-tris(propan-2-yl)benzene-1-sulfonate

Base Information

• Chemical Name: 1-[(1R,2R,3aR,9aS)-5'-oxo-6,6,8,8-tetrakis(propan-2-yl)-hexahydrospiro[furo[3,2-f][1,3,5,2,4]trioxadisilocine-1,2-pyrrolidine]-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl 2,4,6-tris(propan-2-yl)benzene-1-sulfonate
• CAS No.: 1616261-88-1
• Molecular Formula: C₃₉H₆₃N₃O₉SSi₂
• Molecular Weight: 806.181
• Mol file: 1616261-88-1.mol

Synonyms:1-[(1R,2R,3aR,9aS)-5'-oxo-6,6,8,8-tetrakis(propan-2-yl)-hexahydrospiro[furo[3,2-f][1,3,5,2,4]trioxadisilocine-1,2-pyrrolidine]-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl 2,4,6-tris(propan-2-yl)benzene-1-sulfonate

Chemical Property of 1-[(1R,2R,3aR,9aS)-5'-oxo-6,6,8,8-tetrakis(propan-2-yl)-hexahydrospiro[furo[3,2-f][1,3,5,2,4]trioxadisilocine-1,2-pyrrolidine]-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl 2,4,6-tris(propan-2-yl)benzene-1-sulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(1R,2R,3aR,9aS)-5'-oxo-6,6,8,8-tetrakis(propan-2-yl)-hexahydrospiro[furo[3,2-f][1,3,5,2,4]trioxadisilocine-1,2-pyrrolidine]-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl 2,4,6-tris(propan-2-yl)benzene-1-sulfonate

There total 6 articles about 1-[(1R,2R,3aR,9aS)-5'-oxo-6,6,8,8-tetrakis(propan-2-yl)-hexahydrospiro[furo[3,2-f][1,3,5,2,4]trioxadisilocine-1,2-pyrrolidine]-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl 2,4,6-tris(propan-2-yl)benzene-1-sulfonate 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: 67.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + 1-[(1R,2R,3aR,9aS)-5-oxo-6,6,8,8-tetrakis(propan-2-yl)hexahydrospiro[furo[3,2-f][1,3,5,2,4]trioxadisilocine-1,2-yrrolidine]-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione (1616261-86-9) → 1-[(1R,2R,3aR,9aS)-5'-oxo-6,6,8,8-tetrakis(propan-2-yl)-hexahydrospiro[furo[3,2-f][1,3,5,2,4]trioxadisilocine-1,2-pyrrolidine]-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl 2,4,6-tris(propan-2-yl)benzene-1-sulfonate (1616261-88-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 15 ℃; for 1h; regioselective reaction;

DOI:10.1016/j.tetlet.2014.05.051

Reference yield:

1-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione (84828-97-7) → 1-[(1R,2R,3aR,9aS)-5'-oxo-6,6,8,8-tetrakis(propan-2-yl)-hexahydrospiro[furo[3,2-f][1,3,5,2,4]trioxadisilocine-1,2-pyrrolidine]-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl 2,4,6-tris(propan-2-yl)benzene-1-sulfonate (1616261-88-1)

Guidance literature:

Multi-step reaction with 6 steps

1: lithium diisopropyl amide / tetrahydrofuran / 12.17 h / -70 - 25 °C / Inert atmosphere

2: 15-crown-5; sodium azide / N,N-dimethyl-formamide / 2 h / 30 °C

3: dichloromethane / 2 h / 35 °C

4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 3 h / 25 °C

5: acetic acid / ethyl acetate / 2 h / 25 °C

6: triethylamine; dmap / dichloromethane / 1 h / 15 °C

With dmap; sodium azide; 15-crown-5; palladium 10% on activated carbon; hydrogen; acetic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 3: |Wittig Olefination;

DOI:10.1016/j.tetlet.2014.05.051

Reference yield:

ethyl 3-[(6aR,8R,9R,9aS)-9-amino-8-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-2,2,4,4-tetrakis(propan-2-yl)-hexahydro-2H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl]propanoate → 1-[(1R,2R,3aR,9aS)-5'-oxo-6,6,8,8-tetrakis(propan-2-yl)-hexahydrospiro[furo[3,2-f][1,3,5,2,4]trioxadisilocine-1,2-pyrrolidine]-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl 2,4,6-tris(propan-2-yl)benzene-1-sulfonate (1616261-88-1)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / ethyl acetate / 2 h / 25 °C

2: triethylamine; dmap / dichloromethane / 1 h / 15 °C

With dmap; acetic acid; triethylamine; In dichloromethane; ethyl acetate;

DOI:10.1016/j.tetlet.2014.05.051

upstream raw materials:

1-((6aR,8R,9aR)-2,2,4,4-tetraisopropyl-9-oxotetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)pyrimidine-2,4(1H,3H)-dione

1-[(1S,2R,3aR,9aR)-3'-chloro-6,6,8,8-tetrakis(propan-2-yl)-hexahydrospiro[furo[3,2-f][1,3,5,2,4]trioxadisilocine-1,2'-oxirane]-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

(6aR,8R,9R,9aS)-9-azido-8-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-2,2,4,4-tetrakis(propan-2-yl)-hexahydro-2H-furo[3,2-f][1,3,5,2,4]trioxadisilocine-9-carbaldehyde

ethyl (2E)-3-[(6aR,8R,9R,9aS)-9-azido-8-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-2,2,4,4-tetrakis(propan-2-yl)hexahydro-2H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl]prop-2-enoate