5'-<3'-(2''-hydroxyethyl)-4'-trimethylsilyl-2'-oxacyclopentyl>-4-t-butyldiphenylsilyl-oxy-2-thyminyl-1-oxacyclopentane

Base Information

• Chemical Name: 5'-<3'-(2''-hydroxyethyl)-4'-trimethylsilyl-2'-oxacyclopentyl>-4-t-butyldiphenylsilyl-oxy-2-thyminyl-1-oxacyclopentane
• CAS No.: 224177-27-9
• Molecular Formula: C₃₄H₄₈N₂O₆Si₂
• Molecular Weight: 636.936
• Mol file: 224177-27-9.mol

Synonyms:5'-<3'-(2''-hydroxyethyl)-4'-trimethylsilyl-2'-oxacyclopentyl>-4-t-butyldiphenylsilyl-oxy-2-thyminyl-1-oxacyclopentane

Chemical Property of 5'-<3'-(2''-hydroxyethyl)-4'-trimethylsilyl-2'-oxacyclopentyl>-4-t-butyldiphenylsilyl-oxy-2-thyminyl-1-oxacyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-<3'-(2''-hydroxyethyl)-4'-trimethylsilyl-2'-oxacyclopentyl>-4-t-butyldiphenylsilyl-oxy-2-thyminyl-1-oxacyclopentane

There total 2 articles about 5'-<3'-(2''-hydroxyethyl)-4'-trimethylsilyl-2'-oxacyclopentyl>-4-t-butyldiphenylsilyl-oxy-2-thyminyl-1-oxacyclopentane 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: 7.0%

ω-tertbutyldimethyl-silyloxyallyltrimethylsilane (116264-65-4) + 1-(2-deoxy-3-O-tert-butyldiphenylsilyl-β-D-erythro-pentadialdo-1,4-furanosyl)-5-methyluracil (146604-43-5) → 3'-O-tert-butyldiphenylsilyl-5'-C(R)-(5''-hydroxy-2''-pentenyl)thymidine (224157-49-7) + 5'-<3'-(2''-hydroxyethyl)-4'-trimethylsilyl-2'-oxacyclopentyl>-4-t-butyldiphenylsilyl-oxy-2-thyminyl-1-oxacyclopentane (224177-27-9) + 5'-<(5''-trimethylsilyl-2''-oxacyclopentyl)>methyl-3'-O-(t-butyldiphenylsilyl)-thymidine + 3'-O-(t-butyldiphenylsilyl)-5'-C-(3-(3-t-butyldimethylsilyloxy-2-trimethylsilyl)-2-oxetanyl)-thymidine

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; Further byproducts given; 1.) -78 deg C, 3 h, 2.) -78 deg C -> room temperature;

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

Reference yield: 6.0%

ω-tertbutyldimethyl-silyloxyallyltrimethylsilane (116264-65-4) + 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-(pent-3-ene-1-ol)-thymidine + 5'-<3'-(2''-hydroxyethyl)-4'-trimethylsilyl-2'-oxacyclopentyl>-4-t-butyldiphenylsilyl-oxy-2-thyminyl-1-oxacyclopentane (224177-27-9) + 5'-<(5''-trimethylsilyl-2''-oxacyclopentyl)>methyl-3'-O-(t-butyldiphenylsilyl)-thymidine + 3'-O-(t-butyldiphenylsilyl)-5'-C-(3-(3-t-butyldimethylsilyloxy-2-trimethylsilyl)-2-oxetanyl)-thymidine

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; Further byproducts given; 1.) -78 deg C, 3 h, 2.) -78 deg C -> room temperature;

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

Reference yield: 99.0%

5'-<3'-(2''-hydroxyethyl)-4'-trimethylsilyl-2'-oxacyclopentyl>-4-t-butyldiphenylsilyl-oxy-2-thyminyl-1-oxacyclopentane (224177-27-9) → 3'-O-tert-butyldiphenylsilyl-5'-C(R)-(5''-hydroxy-2''-pentenyl)thymidine (224157-49-7)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1002/1099-0690(200112)2001:24<4693::AID-EJOC4693>3.0.CO;2-J

upstream raw materials:

ω-tertbutyldimethyl-silyloxyallyltrimethylsilane

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

Downstream raw materials:

3'-O-tert-butyldiphenylsilyl-5'-C(R)-(5''-hydroxy-2''-pentenyl)thymidine