N⁴-acetyl-1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentafuranosyl>cytosine

Base Information

• Chemical Name: N⁴-acetyl-1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentafuranosyl>cytosine
• CAS No.: 132336-19-7
• Molecular Formula: C₃₃H₃₇N₃O₄SSi
• Molecular Weight: 599.826
• Mol file: 132336-19-7.mol

Synonyms:N⁴-acetyl-1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentafuranosyl>cytosine

Chemical Property of N⁴-acetyl-1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentafuranosyl>cytosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-acetyl-1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentafuranosyl>cytosine

There total 10 articles about N⁴-acetyl-1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentafuranosyl>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: 93.0%

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-D-erythro-pentofuranose (132436-48-7) + 4-(N-trimethylsilylacetamido)-2-trimethylsiloxypyrimidine (18027-23-1) → N4-acetyl-1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentafuranosyl>cytosine (132336-19-7) + N4-acetyl-1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>cytosine (132336-20-0)

Guidance literature:

tin(IV) chloride; In 1,2-dichloro-ethane; at 0 ℃; for 4h; Title compound not separated from byproducts;

DOI:10.1246/cl.1990.1459

Reference yield: 81.0%

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-D-erythro-pentofuranose (132436-48-7) + N4-acetyl-O-trimethylsilylcytosine (54230-57-8) → N4-acetyl-1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentafuranosyl>cytosine (132336-19-7) + N4-acetyl-1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>cytosine (132336-20-0)

Guidance literature:

With tin(IV) chloride; In 1,2-dichloro-ethane; at 0 ℃; for 4h; Yield given. Title compound not separated from byproducts;

DOI:10.3987/COM-91-5884

Reference yield:

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one (102717-29-3) → N4-acetyl-1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentafuranosyl>cytosine (132336-19-7)

Guidance literature:

Multi-step reaction with 3 steps

1: DIBAL-H / toluene / -78 °C

2: NEt₃, SOCl₂ / CH₂Cl₂ / 0 - 25 °C

3: 2) SnCl₄ / 1) CH₂Cl₂, -78 deg C, 30 min, 2) -78 deg C to room temperature, 2 h

With thionyl chloride; tin(IV) chloride; diisobutylaluminium hydride; triethylamine; In dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)74036-6

upstream raw materials:

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-D-erythro-pentofuranose

N⁴-acetyl-O-trimethylsilylcytosine

4-(N-trimethylsilylacetamido)-2-trimethylsiloxypyrimidine

(1S)-1-<<(tert-butyldiphenylsilyl)oxy>methyl>-2,3-dihydrofuran