2,4(1H,3H)-Pyrimidinedione, 1-[(2R,4S,5R)-5-[(1S,3E)-6-bromo-1-hydroxy-3-hexenyl]-4-[[(1,1-dimeth ylethyl)diphenylsilyl]oxy]tetrahydro-2-furanyl]-5-methyl-

Base Information

• Chemical Name: 2,4(1H,3H)-Pyrimidinedione, 1-[(2R,4S,5R)-5-[(1S,3E)-6-bromo-1-hydroxy-3-hexenyl]-4-[[(1,1-dimeth ylethyl)diphenylsilyl]oxy]tetrahydro-2-furanyl]-5-methyl-
• CAS No.: 224157-50-0
• Molecular Formula: C31H39BrN2O5Si
• Molecular Weight: 627.651
• Mol file: 224157-50-0.mol

Synonyms:

Chemical Property of 2,4(1H,3H)-Pyrimidinedione, 1-[(2R,4S,5R)-5-[(1S,3E)-6-bromo-1-hydroxy-3-hexenyl]-4-[[(1,1-dimeth ylethyl)diphenylsilyl]oxy]tetrahydro-2-furanyl]-5-methyl-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4(1H,3H)-Pyrimidinedione, 1-[(2R,4S,5R)-5-[(1S,3E)-6-bromo-1-hydroxy-3-hexenyl]-4-[[(1,1-dimeth ylethyl)diphenylsilyl]oxy]tetrahydro-2-furanyl]-5-methyl-

There total 3 articles about 2,4(1H,3H)-Pyrimidinedione, 1-[(2R,4S,5R)-5-[(1S,3E)-6-bromo-1-hydroxy-3-hexenyl]-4-[[(1,1-dimeth ylethyl)diphenylsilyl]oxy]tetrahydro-2-furanyl]-5-methyl- 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%

5-<3'-(2''-bromoethyl)-4'-trimethylsilyl-2'-oxacyclopentyl>-4-t-butyldiphenylsilyloxy-2-thyminyl-1-oxacyclopentane (224177-29-1) → 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(bromo-1-pent-3-ene)-thymidine (224157-50-0)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4020(99)00246-X

Reference yield:

ω-bromo-allyltrimethylsilane (126016-59-9) + 1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil (146604-43-5) → 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(bromo-1-pent-3-ene)-thymidine (224157-50-0) + 5-<3'-(2''-bromoethyl)-4'-trimethylsilyl-2'-oxacyclopentyl>-4-t-butyldiphenylsilyloxy-2-thyminyl-1-oxacyclopentane (224177-29-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - 20 ℃; for 4h;

DOI:10.1016/S0040-4020(99)00246-X

Reference yield:

1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil (146604-43-5) → 3'-O-(t-butyldiphenylsilyl)-(5S)'-C-(bromo-1-pent-3-ene)-thymidine (224157-50-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 513 mg / BF₃*Et₂O / CH₂Cl₂ / 4 h / -78 - 20 °C

2: 100 percent / TiCl₄ / CH₂Cl₂ / 0 °C

With boron trifluoride diethyl etherate; titanium tetrachloride; In dichloromethane;

DOI:10.1016/S0040-4020(99)00246-X

upstream raw materials:

ω-bromo-allyltrimethylsilane

1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil

5-<3'-(2''-bromoethyl)-4'-trimethylsilyl-2'-oxacyclopentyl>-4-t-butyldiphenylsilyloxy-2-thyminyl-1-oxacyclopentane