1-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-4-N-benzoylcytosine

Base Information

• Chemical Name: 1-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-4-N-benzoylcytosine
• CAS No.: 848644-38-2
• Molecular Formula: C₂₄H₂₃N₃O₉
• Molecular Weight: 497.461
• Mol file: 848644-38-2.mol

Synonyms:1-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-4-N-benzoylcytosine

Chemical Property of 1-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-4-N-benzoylcytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-4-N-benzoylcytosine

There total 7 articles about 1-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-4-N-benzoylcytosine 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: 71.0%

1,2,3,5-tetra-O-acetyl-3-C-ethynyl-D-ribo-pentofuranose (848644-37-1) + 4-N-benzoylcytosine (26661-13-2) → 1-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-4-N-benzoylcytosine (848644-38-2)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 60 ℃; for 24h;

DOI:10.1016/j.bmc.2004.11.054

Reference yield:

Acetic acid (2R,3S,4R)-2-acetoxymethyl-3-ethynyl-4,5-dihydroxy-tetrahydro-furan-3-yl ester → 1-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-4-N-benzoylcytosine (848644-38-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 5.84 g / pyridine; 4-(dimethylamino)pyridine / 40 h / 20 °C

2: 71 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 24 h / 60 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile;

DOI:10.1016/j.bmc.2004.11.054

Reference yield:

Acetic acid (3aR,5R,6R,6aR)-5-acetoxymethyl-6-ethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (861444-58-8) → 1-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-4-N-benzoylcytosine (848644-38-2)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / H₂O / 6 h / 20 °C

2: 5.84 g / pyridine; 4-(dimethylamino)pyridine / 40 h / 20 °C

3: 71 percent / N,O-bis(trimethylsilyl)acetamide; trimethylsilyl triflate / acetonitrile / 24 h / 60 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In water; acetonitrile;

DOI:10.1016/j.bmc.2004.11.054

upstream raw materials:

1,2,3,5-tetra-O-acetyl-3-C-ethynyl-D-ribo-pentofuranose

4-N-benzoylcytosine

Acetic acid (3aR,5R,6R,6aR)-5-acetoxymethyl-6-ethynyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

3-C-ethynyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

Downstream raw materials:

3'-ethynylcytidine

Refernces