1-[3,3-bis({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methyl-isoxazolidin-5-yl]-5-fluoropyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-[3,3-bis({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methyl-isoxazolidin-5-yl]-5-fluoropyrimidine-2,4(1H,3H)-dione
• CAS No.: 736153-51-8
• Molecular Formula: C₂₂H₄₂FN₃O₅Si₂
• Molecular Weight: 503.762
• Mol file: 736153-51-8.mol

Synonyms:

Chemical Property of 1-[3,3-bis({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methyl-isoxazolidin-5-yl]-5-fluoropyrimidine-2,4(1H,3H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[3,3-bis({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methyl-isoxazolidin-5-yl]-5-fluoropyrimidine-2,4(1H,3H)-dione

There total 3 articles about 1-[3,3-bis({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methyl-isoxazolidin-5-yl]-5-fluoropyrimidine-2,4(1H,3H)-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: 55.0%

3,3-bis({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methyl-isoxazolidin-5-yl acetate (736153-41-6) + 5-fluorouracil (51-21-8) → 1-[3,3-bis({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methyl-isoxazolidin-5-yl]-5-fluoropyrimidine-2,4(1H,3H)-dione (736153-51-8)

Guidance literature:

5-fluorouracil; With bis-(trimethylsilyl)acetamide; In acetonitrile; for 0.25h; Heating;

3,3-bis({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methyl-isoxazolidin-5-yl acetate; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2004.04.041

Reference yield:

[2-{[tert-butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethylidene](methyl)azane oxide (736153-35-8) → 1-[3,3-bis({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methyl-isoxazolidin-5-yl]-5-fluoropyrimidine-2,4(1H,3H)-dione (736153-51-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / 36 h / 20 °C

2.1: bis(trimethylsilyl)acetamide / acetonitrile / 0.25 h / Heating

2.2: 55 percent / trimethylsilyl triflate / acetonitrile / 12 h / 20 °C

With bis-(trimethylsilyl)acetamide; In acetonitrile;

DOI:10.1016/j.bmc.2004.04.041

Reference yield:

1,3-bis-O-(tert-butyldimethylsilyl)-1,3-dihydroxy-2-propanone (127382-65-4) → 1-[3,3-bis({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methyl-isoxazolidin-5-yl]-5-fluoropyrimidine-2,4(1H,3H)-dione (736153-51-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 90 percent / Et₃N / toluene / 3 h / 20 °C

2.1: 85 percent / 36 h / 20 °C

3.1: bis(trimethylsilyl)acetamide / acetonitrile / 0.25 h / Heating

3.2: 55 percent / trimethylsilyl triflate / acetonitrile / 12 h / 20 °C

With bis-(trimethylsilyl)acetamide; triethylamine; In toluene; acetonitrile;

DOI:10.1016/j.bmc.2004.04.041

upstream raw materials:

3,3-bis({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methyl-isoxazolidin-5-yl acetate

5-fluorouracil

[2-{[tert-butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethylidene](methyl)azane oxide

1,3-bis-O-(tert-butyldimethylsilyl)-1,3-dihydroxy-2-propanone