N-3-tert-butoxycarbonyl-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylidene-β-D-ribo-(5S)-hexofuranosyl)uracil

Base Information

• Chemical Name: N-3-tert-butoxycarbonyl-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylidene-β-D-ribo-(5S)-hexofuranosyl)uracil
• CAS No.: 1454611-85-8
• Molecular Formula: C₃₆H₄₃N₂O₁₃PS₂
• Molecular Weight: 806.849
• Mol file: 1454611-85-8.mol

Synonyms:N-3-tert-butoxycarbonyl-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylidene-β-D-ribo-(5S)-hexofuranosyl)uracil

Chemical Property of N-3-tert-butoxycarbonyl-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylidene-β-D-ribo-(5S)-hexofuranosyl)uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-3-tert-butoxycarbonyl-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylidene-β-D-ribo-(5S)-hexofuranosyl)uracil

There total 8 articles about N-3-tert-butoxycarbonyl-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylidene-β-D-ribo-(5S)-hexofuranosyl)uracil 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: 33.0%

N-3-tert-butoxycarbonyl-1-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuranosyl)uracil (1454611-75-6) + bis(phenyl)S-acyl-2-thioethyl H-phosphonate (194612-85-6) → N-3-tert-butoxycarbonyl-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylidene-β-D-ribo-(5S)-hexofuranosyl)uracil (1454611-85-8)

Guidance literature:

bis(phenyl)S-acyl-2-thioethyl H-phosphonate; With chloro-trimethyl-silane; triethylamine; In toluene; at 20 ℃; for 3h; Inert atmosphere;

N-3-tert-butoxycarbonyl-1-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuranosyl)uracil; With boron trifluoride diethyl etherate; In dichloromethane; toluene; at -60 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol402143y

Reference yield:

1-(2,3-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)uracil (174498-64-7) → N-3-tert-butoxycarbonyl-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylidene-β-D-ribo-(5S)-hexofuranosyl)uracil (1454611-85-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / 6 h / 0 °C / Inert atmosphere

2.1: potassium carbonate / methanol / 0 - 20 °C

3.1: triethylamine; dmap / tetrahydrofuran / 1.25 h / 20 °C

4.1: triethylamine; chloro-trimethyl-silane / toluene / 3 h / 20 °C / Inert atmosphere

4.2: -60 - 20 °C / Inert atmosphere

With pyridine; dmap; chloro-trimethyl-silane; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; toluene;

DOI:10.1021/ol402143y

Reference yield:

S-(2-hydroxyethyl) thiobenzoate (52772-11-9) → N-3-tert-butoxycarbonyl-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylidene-β-D-ribo-(5S)-hexofuranosyl)uracil (1454611-85-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; phosphorus trichloride / diethyl ether / 0 - 20 °C / Inert atmosphere; Reflux

2.1: triethylamine; chloro-trimethyl-silane / toluene / 3 h / 20 °C / Inert atmosphere

2.2: -60 - 20 °C / Inert atmosphere

With chloro-trimethyl-silane; triethylamine; phosphorus trichloride; In diethyl ether; toluene;

DOI:10.1021/ol402143y

upstream raw materials:

1-(2,3:5,6-di-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)uracil

1-(2,3-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)uracil

1-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuranosyl)uracil

N-3-tert-butoxycarbonyl-1-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuranosyl)uracil

Downstream raw materials:

1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-β-D-ribo-(5S)-hexofuranosyl)uracil