2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine

Base Information

• Chemical Name: 2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine
• CAS No.: 101527-55-3
• Molecular Formula: C₂₉H₂₈N₂O₇S
• Molecular Weight: 548.617
• Mol file: 101527-55-3.mol

Synonyms:2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine

Chemical Property of 2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine

There total 4 articles about 2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine 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: 100.0%

2',3'-di-O-mesyl-5'-O-trityl-2',3'-seco-uridine (101552-16-3) → 2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine (101527-55-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1002/hlca.19920750209

Reference yield:

1-(2-hydroxy-1-{[1-hydroxy-3-(triphenylmethoxy)propan-2-yl]oxy}ethyl)pyrimidine-2,4(1H,3H)-dione (101527-47-3) → 2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine (101527-55-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / acetone / Ambient temperature

2: Et₃N / acetone / 21 h

With triethylamine; In acetone;

DOI:10.1080/07328319808003475

Reference yield:

5'-O-trityluridine (6554-10-5) → 2,2'-anhydro-3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine (101527-55-3)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium periodate / 1,4-dioxane; water / 2 h / 20 °C / Inert atmosphere; Darkness

2: sodium tetrahydroborate / 1,4-dioxane / 0.5 h / 20 °C / Inert atmosphere

3: triethylamine / dichloromethane / 0 °C / Inert atmosphere

4: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; sodium periodate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1002/hlca.201300289

upstream raw materials:

2',3'-di-O-mesyl-5'-O-trityl-2',3'-seco-uridine

1-(2-hydroxy-1-{[1-hydroxy-3-(triphenylmethoxy)propan-2-yl]oxy}ethyl)pyrimidine-2,4(1H,3H)-dione

5'-O-trityluridine

Downstream raw materials:

1-(R)-<6-(R)-trityloxymethyl-1,4-dioxan-2-yl>uracil

3'-O-(methylsulfonyl)-5'-O-(triphenylmethyl)-2',3'-secouridine

Methanesulfonic acid (R)-2-[(R)-1-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-phenylselanyl-ethoxy]-3-trityloxy-propyl ester

2-[2-azido-1-(3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl)ethoxy]-3-(triphenylmethoxy)propyl benzoate