N-4-di(tert-butoxycarbonyl)-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylid-ene-β-D-ribo-(5S)-hexofuranosyl)cytosine

Base Information

• Chemical Name: N-4-di(tert-butoxycarbonyl)-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylid-ene-β-D-ribo-(5S)-hexofuranosyl)cytosine
• CAS No.: 1454611-86-9
• Molecular Formula: C₄₁H₅₂N₃O₁₄PS₂
• Molecular Weight: 905.981
• Mol file: 1454611-86-9.mol

Synonyms:N-4-di(tert-butoxycarbonyl)-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylid-ene-β-D-ribo-(5S)-hexofuranosyl)cytosine

Chemical Property of N-4-di(tert-butoxycarbonyl)-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylid-ene-β-D-ribo-(5S)-hexofuranosyl)cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-4-di(tert-butoxycarbonyl)-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylid-ene-β-D-ribo-(5S)-hexofuranosyl)cytosine

There total 2 articles about N-4-di(tert-butoxycarbonyl)-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylid-ene-β-D-ribo-(5S)-hexofuranosyl)cytosine 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,N-4(ditert-butoxycarbonyl)-1-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuranosyl)cytosine (1454611-81-4) + bis(phenyl)S-acyl-2-thioethyl H-phosphonate (194612-85-6) → N-4-di(tert-butoxycarbonyl)-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylid-ene-β-D-ribo-(5S)-hexofuranosyl)cytosine (1454611-86-9)

Guidance literature:

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

N,N-4(ditert-butoxycarbonyl)-1-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuranosyl)cytosine; With boron trifluoride diethyl etherate; In dichloromethane; toluene; at -60 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol402143y

Reference yield:

N,N-4(ditert-butoxycarbonyl)-1-(2,3-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)cytosine (1454612-00-0) → N-4-di(tert-butoxycarbonyl)-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylid-ene-β-D-ribo-(5S)-hexofuranosyl)cytosine (1454611-86-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diethylazodicarboxylate; triphenylphosphine / toluene / 4 h / 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; triphenylphosphine; diethylazodicarboxylate; In toluene;

DOI:10.1021/ol402143y

Reference yield: 62.0%

N-4-di(tert-butoxycarbonyl)-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylid-ene-β-D-ribo-(5S)-hexofuranosyl)cytosine (1454611-86-9) → 1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-β-D-ribo-(5S)-hexofuranosyl)cytosine (1454611-88-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 4h;

DOI:10.1021/ol402143y

upstream raw materials:

N,N-4(ditert-butoxycarbonyl)-1-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuranosyl)cytosine

bis(phenyl)S-acyl-2-thioethyl H-phosphonate

N,N-4(ditert-butoxycarbonyl)-1-(2,3-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)cytosine

Downstream raw materials:

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