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

Base Information

• Chemical Name: 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
• CAS No.: 95919-36-1
• Molecular Formula: C₄₆H₅₄N₆O₂₄P₂
• Molecular Weight: 1136.91
• Mol file: 95919-36-1.mol

Synonyms:

Chemical Property of 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

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

There total 13 articles about 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 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')-3'-deoxy-3'dihydroxyphosphinylmethyl-2'-O-acetyl uridylyl-(3'<*>5')-2',3'-O-isopropylidene uridine (95919-36-1)

Guidance literature:

Multi-step reaction with 13 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

12: 50 percent / 98percent hydrazine hydrate / pyridine; acetic acid / 24 h / Ambient temperature

13: 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; hydrazine hydrate; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; tin(ll) chloride; In pyridine; methanol; chloroform; water; acetic acid; 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')-3'-deoxy-3'dihydroxyphosphinylmethyl-2'-O-acetyl uridylyl-(3'<*>5')-2',3'-O-isopropylidene uridine (95919-36-1)

Guidance literature:

Multi-step reaction with 12 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

11: 50 percent / 98percent hydrazine hydrate / pyridine; acetic acid / 24 h / Ambient temperature

12: 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; hydrazine hydrate; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; tin(ll) chloride; In pyridine; methanol; chloroform; water; acetic acid; 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')-3'-deoxy-3'dihydroxyphosphinylmethyl-2'-O-acetyl uridylyl-(3'<*>5')-2',3'-O-isopropylidene uridine (95919-36-1)

Guidance literature:

Multi-step reaction with 9 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

8: 50 percent / 98percent hydrazine hydrate / pyridine; acetic acid / 24 h / Ambient temperature

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

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

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

upstream raw materials:

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

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