5-bromo-1-[5,6-di-O-acetyl-2,3-dideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-alpha-D-arabino-hexofuranosyl]pyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 5-bromo-1-[5,6-di-O-acetyl-2,3-dideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-alpha-D-arabino-hexofuranosyl]pyrimidine-2,4(1H,3H)-dione
• CAS No.: 133488-22-9
• Molecular Formula: C₂₂H₂₀BrN₃O₉
• Molecular Weight: 550.319
• Mol file: 133488-22-9.mol

Synonyms:

Chemical Property of 5-bromo-1-[5,6-di-O-acetyl-2,3-dideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-alpha-D-arabino-hexofuranosyl]pyrimidine-2,4(1H,3H)-dione

Chemical Property:

• Density: 1.665g/cm³

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-bromo-1-[5,6-di-O-acetyl-2,3-dideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-alpha-D-arabino-hexofuranosyl]pyrimidine-2,4(1H,3H)-dione

There total 2 articles about 5-bromo-1-[5,6-di-O-acetyl-2,3-dideoxy-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-alpha-D-arabino-hexofuranosyl]pyrimidine-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: 48.0%

1,5,6-Tri-O-acetyl-2,3-dideoxy-3-phthalimido-α-D-arabino-hexofuranose (119812-56-5) + 2,4-bis-(trimethylsilyloxy)-5-bromopyrimidine (33282-64-3) → 1-(5,6-Di-O-acetyl-2,3-dideoxy-3-phthalimido-α-D-arabino-hexafuranosyl)-5-bromouracil (133488-22-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -5 - 0 ℃; for 0.5h;

DOI:10.1002/ardp.19913240205

Reference yield:

Acetic acid (R)-2-acetoxy-1-[(S)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-furan-2-yl]-ethyl ester (119812-52-1,119812-53-2,119812-54-3,119812-55-4) → 1-(5,6-Di-O-acetyl-2,3-dideoxy-3-phthalimido-α-D-arabino-hexafuranosyl)-5-bromouracil (133488-22-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 30 percent / pyridine / 6 h / 20 °C

2: 48 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0.5 h / -5 - 0 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; In acetonitrile;

DOI:10.1002/ardp.19913240205

upstream raw materials:

1,5,6-Tri-O-acetyl-2,3-dideoxy-3-phthalimido-α-D-arabino-hexofuranose

2,4-bis-(trimethylsilyloxy)-5-bromopyrimidine

Acetic acid (R)-2-acetoxy-1-[(S)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-furan-2-yl]-ethyl ester