5'-(benzoylpropionyl)-3'-deoxy-3'-diisopropoxyphosphinylmethyl-2'-O-acetyl uridine

Base Information

• Chemical Name: 5'-(benzoylpropionyl)-3'-deoxy-3'-diisopropoxyphosphinylmethyl-2'-O-acetyl uridine
• CAS No.: 95899-93-7
• Molecular Formula: C₂₈H₃₇N₂O₁₁P
• Molecular Weight: 608.582
• Mol file: 95899-93-7.mol

Synonyms:5'-(benzoylpropionyl)-3'-deoxy-3'-diisopropoxyphosphinylmethyl-2'-O-acetyl uridine

Chemical Property of 5'-(benzoylpropionyl)-3'-deoxy-3'-diisopropoxyphosphinylmethyl-2'-O-acetyl uridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-(benzoylpropionyl)-3'-deoxy-3'-diisopropoxyphosphinylmethyl-2'-O-acetyl uridine

There total 9 articles about 5'-(benzoylpropionyl)-3'-deoxy-3'-diisopropoxyphosphinylmethyl-2'-O-acetyl uridine 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: 80.0%

bis(trimethylsilyloxy)pyrimidine (68027-39-4) + 5-(3-benzoylpropionyl)-3-deoxy-3-diisopropoxyphosphinylmethyl-1,2-di-O-acetyl-D-ribofuranose (95899-92-6) → 5'-(benzoylpropionyl)-3'-deoxy-3'-diisopropoxyphosphinylmethyl-2'-O-acetyl uridine (95899-93-7)

Guidance literature:

With tin(ll) chloride; In acetonitrile; for 24h; Ambient temperature;

DOI:10.1016/0040-4020(84)85072-3

Reference yield:

3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methylene-α-D-ribo-hexofuranose (21665-16-7,37776-66-2) → 5'-(benzoylpropionyl)-3'-deoxy-3'-diisopropoxyphosphinylmethyl-2'-O-acetyl uridine (95899-93-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) borane; 2.) 2N NaOH, 30percent hydrogen peroxide / 1.) THF, dimethyl sulfide, 0 deg C, 24 h; 2.) THF, water, 0 deg C - RT, 2 h

2: 73.8 percent / N-bromosuccinimide, triphenylphosphine / dimethylformamide; pyridine / 1.) 0 deg C - RT, 1 h; 2.) 60 deg C, 3 h

3: 91.2 percent / 1.6percent sulfuric acid / methanol; CHCl₃; H₂O / 72 h / Ambient temperature

4: 1.) sodium meta-periodate, sodium bicarbonate; 2.) sodium borohydride / 1.) ethanol, water, RT, 3 h; 2.) RT, overnight

5: 53.5 percent / DCC / pyridine / 24 h / Ambient temperature

6: 80percent acetic acid / H₂O / 24 h / 80 °C

7: pyridine / Ambient temperature

8: 68 percent / 72 h / 160 - 180 °C

9: 80 percent / stannous chloride / acetonitrile / 24 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; sulfuric acid; borane; dihydrogen peroxide; sodium hydrogencarbonate; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; tin(ll) chloride; In pyridine; methanol; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4020(84)85072-3

Reference yield:

3-C-deoxy-3-C-hydroxymethyl-1,2;5,6-di-O-isopropylidene-α-D-allo-furanose (69832-48-0,119100-05-9) → 5'-(benzoylpropionyl)-3'-deoxy-3'-diisopropoxyphosphinylmethyl-2'-O-acetyl uridine (95899-93-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 73.8 percent / N-bromosuccinimide, triphenylphosphine / dimethylformamide; pyridine / 1.) 0 deg C - RT, 1 h; 2.) 60 deg C, 3 h

2: 91.2 percent / 1.6percent sulfuric acid / methanol; CHCl₃; H₂O / 72 h / Ambient temperature

3: 1.) sodium meta-periodate, sodium bicarbonate; 2.) sodium borohydride / 1.) ethanol, water, RT, 3 h; 2.) RT, overnight

4: 53.5 percent / DCC / pyridine / 24 h / Ambient temperature

5: 80percent acetic acid / H₂O / 24 h / 80 °C

6: pyridine / Ambient temperature

7: 68 percent / 72 h / 160 - 180 °C

8: 80 percent / stannous chloride / acetonitrile / 24 h / Ambient temperature

With sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; sulfuric acid; sodium hydrogencarbonate; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; tin(ll) chloride; In pyridine; methanol; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4020(84)85072-3

upstream raw materials:

bis(trimethylsilyloxy)pyrimidine

5-(3-benzoylpropionyl)-3-deoxy-3-diisopropoxyphosphinylmethyl-1,2-di-O-acetyl-D-ribofuranose

3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methylene-α-D-ribo-hexofuranose

3-C-deoxy-3-C-hydroxymethyl-1,2;5,6-di-O-isopropylidene-α-D-allo-furanose

Downstream raw materials:

5'-(3-benzoylpropionyl)-3'-deoxy-3'-dihydroxyphosphinylmethyl-2'-O-acetyl uridine pyridinium salt

5'-O-(3-benzoylpropionyl)-3'-deoxy-3'-dihydroxyphosphinylmethyl-2'-O-acetyl uridylyl-(3'<*>5')-2',3'-O-isopropylidene uridine pyridinium salt

5'-O-(3-benzoylpropionyl)-3'-deoxy-3'-dihydroxyphosphinylmethyl-2'-O-acetyl uridylyl-(3'<*>5')-3'-deoxy-3'dihydroxyphosphinylmethyl-2'-O-acetyl uridylyl-(3'<*>5')-2',3'-O-isopropylidene uridine