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

Base Information

• Chemical Name: 5'-O-(3-benzoylpropionyl)-3'-deoxy-3'-dihydroxyphosphinylmethyl-2'-O-acetyl uridylyl-(3'<*>5')-2',3'-O-isopropylidene uridine pyridinium salt
• CAS No.: 95899-97-1
• Molecular Formula: C₅H₅N*C₃₄H₃₉N₄O₁₆P
• Molecular Weight: 869.776
• Mol file: 95899-97-1.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 5'-O-(3-benzoylpropionyl)-3'-deoxy-3'-dihydroxyphosphinylmethyl-2'-O-acetyl uridylyl-(3'<*>5')-2',3'-O-isopropylidene uridine pyridinium salt 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:

3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methylene-α-D-ribo-hexofuranose (21665-16-7,37776-66-2) → 5'-O-(3-benzoylpropionyl)-3'-deoxy-3'-dihydroxyphosphinylmethyl-2'-O-acetyl uridylyl-(3'<*>5')-2',3'-O-isopropylidene uridine pyridinium salt (95899-97-1)

Guidance literature:

Multi-step reaction with 11 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

10: 1.) trimethylsilyl bromide; 2.) pyridine / 1.) chloroform, 7 h; 2.) water, 1 h

11: 1.) DOWEX 50 (pyridinium form); 2.) DCC / 2.) pyridine, RT, 6 days

With pyridine; sodium hydroxide; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; trimethylsilyl bromide; DOWEX 50 (pyridinium form); 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'-O-(3-benzoylpropionyl)-3'-deoxy-3'-dihydroxyphosphinylmethyl-2'-O-acetyl uridylyl-(3'<*>5')-2',3'-O-isopropylidene uridine pyridinium salt (95899-97-1)

Guidance literature:

Multi-step reaction with 10 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

9: 1.) trimethylsilyl bromide; 2.) pyridine / 1.) chloroform, 7 h; 2.) water, 1 h

10: 1.) DOWEX 50 (pyridinium form); 2.) DCC / 2.) pyridine, RT, 6 days

With pyridine; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; trimethylsilyl bromide; DOWEX 50 (pyridinium form); 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

Reference yield:

3-deoxy-3-bromomethyl-1,2-O-isopropylidene-α-D-ribofuranose (95899-89-1) → 5'-O-(3-benzoylpropionyl)-3'-deoxy-3'-dihydroxyphosphinylmethyl-2'-O-acetyl uridylyl-(3'<*>5')-2',3'-O-isopropylidene uridine pyridinium salt (95899-97-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 53.5 percent / DCC / pyridine / 24 h / Ambient temperature

2: 80percent acetic acid / H₂O / 24 h / 80 °C

3: pyridine / Ambient temperature

4: 68 percent / 72 h / 160 - 180 °C

5: 80 percent / stannous chloride / acetonitrile / 24 h / Ambient temperature

6: 1.) trimethylsilyl bromide; 2.) pyridine / 1.) chloroform, 7 h; 2.) water, 1 h

7: 1.) DOWEX 50 (pyridinium form); 2.) DCC / 2.) pyridine, RT, 6 days

With pyridine; trimethylsilyl bromide; DOWEX 50 (pyridinium form); acetic acid; dicyclohexyl-carbodiimide; tin(ll) chloride; In pyridine; water; acetonitrile;

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

upstream raw materials:

2',3'-O-isopropylideneuridine

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

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'-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