1-(2,3-anhydro-5-O-trityl-beta-D-glycero-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-(2,3-anhydro-5-O-trityl-beta-D-glycero-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS No.: 115913-84-3
• Molecular Formula: C29H26 N2 O5
• Molecular Weight: 482.536
• Mol file: 115913-84-3.mol

Synonyms:3,6-Dioxabicyclo[3.1.0]hexane,2,4(1H,3H)-pyrimidinedione deriv.

Chemical Property of 1-(2,3-anhydro-5-O-trityl-beta-D-glycero-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Chemical Property:

• Melting Point: 174-175 °C
• PKA: 9.44±0.10(Predicted)
• PSA: 86.11000
• Density: 1.294g/cm³
• LogP: 3.93080

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(2,3-anhydro-5-O-trityl-beta-D-glycero-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione

There total 12 articles about 1-(2,3-anhydro-5-O-trityl-beta-D-glycero-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione 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: 99.0%

5-methyl-5'-O-(triphenylmethyl)uridine 2',3'-bis(methanesulfonate) (124493-84-1) → 1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine (115913-84-3)

Guidance literature:

With sodium hydroxide; In water; acetone; at 20 ℃; for 18h;

DOI:10.1021/jm100165w

Reference yield: 93.0%

2,2'-anhydro-1-(3'-deoxy-3'-bromo-5'-O-trityl-β-D-arabinofuranosyl)thymine (145819-53-0) → 1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine (115913-84-3)

Guidance literature:

With sodium hydroxide; In acetone; for 0.333333h;

Reference yield: 35.4%

1-(2,3-anhydro-5-O-trityl-β-D-lyxofuranosyl)-2-O-methylthymine (142545-13-9) → 1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine (115913-84-3) + 2,2'-anhydro-1-(3'-deoxy-3'-bromo-5'-O-trityl-β-D-arabinofuranosyl)thymine (145819-53-0) + 1-(2,3-anhydro-5-O-trityl-β-D-lyxofuranosyl)-N3-methylthymine

Guidance literature:

With lithium bromide; In tetrahydrofuran; for 115h; Ambient temperature;

DOI:10.1080/07328319308016204

upstream raw materials:

5-methyl-5'-O-(triphenylmethyl)uridine 2',3'-bis(methanesulfonate)

2,2'-anhydro-1-(3'-deoxy-3'-bromo-5'-O-trityl-β-D-arabinofuranosyl)thymine

1-(2,3-anhydro-5-O-trityl-β-D-lyxofuranosyl)-2-O-methylthymine

1-(5'-O-trityl-β-D-ribofuranosyl)thymine

Downstream raw materials:

1-[(2R,3S,4S,5S)-3-Hydroxy-4-(5-methyl-[1,3,5]dithiazinan-2-yl)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

1-(5-O-trityl-3-imidazol-1-yl-3-deoxy-β-D-arabinofuranosyl)thymine

1-(3-bromo-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine

1-(2-bromo-2-deoxy-5-O-trityl-β-D-xylofuranosyl)thymine

Refernces

• 1、 Haraguchi, Kazuhiro,Itoh, Yoshiharu,Takeda, Shingo,Honma, Yosuke,Tanaka, Hiromichi,Nitanda, Takao,Baba, Masanori,Dutschman, Ginger E.,Cheng, Yung-Chi. "Synthesis and anti-HIV activity of 4′-cyano-2′,3′ -didehydro-3′-deoxythymidine". . p. 647 - 654. Retrieved 2007/10/03.
• 2、 Watanabe,Yanagihara,Minamoto,Iwasaki. "Reactions of some 2,3-anhydro pyrimidine nucleosides with dilithium tetrahalocuprates". . p. 1061 - 1074. Retrieved 2007/10/02.