1-{2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl}-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-{2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl}-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 290293-17-3
• Molecular Formula: C₃₂H₄₁N₃O₇Si
• Molecular Weight: 607.779

Synonyms:

Chemical Property of 1-{2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl}-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of 1-{2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl}-5-methyl-1H-pyrimidine-2,4-dione

There total 3 articles about 1-{2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl}-5-methyl-1H-pyrimidine-2,4-dione 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: 25.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1-vinylthymine (20245-84-5) + N-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-hydroxylamine → 1-{2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl}-5-methyl-1H-pyrimidine-2,4-dione (290293-17-3) + 1-{2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl}-5-methyl-1H-pyrimidine-2,4-dione (290293-15-1)

Guidance literature:

In chloroform; at 60 ℃;

DOI:10.1021/jm0308186

Reference yield:

Acetic acid 2-[(3aR,4R,6R,6aR)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl ester → 1-{2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl}-5-methyl-1H-pyrimidine-2,4-dione (290293-17-3) + 1-{2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl}-5-methyl-1H-pyrimidine-2,4-dione (290293-15-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 ℃;

DOI:10.1016/S0957-4166(00)00160-9

Reference yield:

C25H33NO5Si → 1-{2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl}-5-methyl-1H-pyrimidine-2,4-dione (290293-17-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 36 h / 70 °C

2: TMSOTf / acetonitrile / 0 °C

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; 1: Cycloaddition / 2: Condensation;

DOI:10.1016/S0957-4166(00)00160-9

upstream raw materials:

formaldehyd

1-vinylthymine

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