1-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-4-chloro-2-deoxy-β-D-threo-pentofuranosyl]thymine

Base Information

• Chemical Name: 1-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-4-chloro-2-deoxy-β-D-threo-pentofuranosyl]thymine
• CAS No.: 897037-31-9
• Molecular Formula: C₂₃H₃₁ClN₂O₆Si
• Molecular Weight: 495.047
• Mol file: 897037-31-9.mol

Synonyms:1-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-4-chloro-2-deoxy-β-D-threo-pentofuranosyl]thymine

Chemical Property of 1-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-4-chloro-2-deoxy-β-D-threo-pentofuranosyl]thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-4-chloro-2-deoxy-β-D-threo-pentofuranosyl]thymine

There total 1 articles about 1-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-4-chloro-2-deoxy-β-D-threo-pentofuranosyl]thymine 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: 53.0%

C30H36N2O8Si (744217-13-8) → 1-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-4-chloro-2-deoxy-α-L-erythro-pentofuranosyl]thymine (897037-32-0) + 1-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-4-chloro-2-deoxy-β-D-threo-pentofuranosyl]thymine (897037-31-9)

Guidance literature:

With methylaluminum dichloride; In hexane; dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jo060194m

Reference yield: 71.0%

1-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-4-chloro-2-deoxy-β-D-threo-pentofuranosyl]thymine (897037-31-9) + ethyl[trimethylsilyl(ethynyl)]aluminum chloride → 1-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-C-(trimethylsilyl)ethynyl-β-D-threo-pentofuranosyl]thymine (744217-14-9)

Guidance literature:

In hexane; dichloromethane; toluene; at 0 - 20 ℃;

DOI:10.1021/jo060194m

Reference yield:

1-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-4-chloro-2-deoxy-β-D-threo-pentofuranosyl]thymine (897037-31-9) → 1-[5-O-benzoyl-2-deoxy-4-C-ethynyl-β-D-threo-pentofuranosyl]thymine (744217-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / toluene; hexane; CH₂Cl₂ / 0 - 20 °C

2: 97 percent / aqueous Bu₄NF / tetrahydrofuran / 1.5 h / 0 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1021/jo060194m

upstream raw materials:

C₃₀H₃₆N₂O₈Si

Downstream raw materials:

1-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-C-(trimethylsilyl)ethynyl-β-D-threo-pentofuranosyl]thymine

1-[5-O-benzoyl-2-deoxy-4-C-ethynyl-β-D-threo-pentofuranosyl]thymine

Benzoic acid (2R,3R,5R)-2-ethynyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-trifluoromethanesulfonyloxy-tetrahydro-furan-2-ylmethyl ester