1-[(1R,4R,5R)-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]-5-methylpyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(1R,4R,5R)-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS No.: 14486-22-7
• Molecular Formula: C₁₀H₁₂N₂O₅
• Molecular Weight: 240.216
• Mol file: 14486-22-7.mol

Synonyms:2',3'-anhydrothymidine;2',3'-LAT;2',3'-lyxoanhydrothymidine

Chemical Property of 1-[(1R,4R,5R)-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]-5-methylpyrimidine-2,4-dione

Chemical Property:

• Melting Point: 143.5-144.5 °C
• PKA: 9.44±0.10(Predicted)
• PSA: 111.61000
• Density: 1.505 g/cm³
• LogP: -0.35320
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol (slightly)
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 240.07462149
• Heavy Atom Count: 17
• Complexity: 421

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2C3C(O3)C(O2)CO
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)C2[C@H]3[C@H](O3)[C@H](O2)CO
• Uses: 2'',3''-Anhydroadenosine is an intermediate in synthesizing Cordycepin (C685800), which is the first reported nucleoside antibiotic.

Technology Process of 1-[(1R,4R,5R)-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]-5-methylpyrimidine-2,4-dione

There total 14 articles about 1-[(1R,4R,5R)-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]-5-methylpyrimidine-2,4-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: 95.0%

5'-O-(4,4'-dimethoxytrityl)-1-(2,3-anhydro-β-D-lyxofuranosyl)thymine (114551-08-5) → 1-(2,3-anhydro-β-D-lyxofuranosyl)thymine (14486-22-7)

Guidance literature:

With acetic acid; at 22 ℃; for 0.5h;

DOI:10.1021/jm00402a038

Reference yield: 85.0%

2,2'-Anhydro-1-(5'-O-Benzoyl-3'-O-methylsulfonyl-β-D-arabinofuranosyl)thymine (99631-18-2) → 1-(2,3-anhydro-β-D-lyxofuranosyl)thymine (14486-22-7)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; acetone; for 16h; Ambient temperature;

DOI:10.1055/s-1988-27760

Reference yield: 62.0%

2,2'-Anhydro-1-(3'-O-methylsulfonyl-β-D-arabinofuranosyl)thymine (120649-60-7) → 1-(2,3-anhydro-β-D-lyxofuranosyl)thymine (14486-22-7)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; acetone; for 16h; Ambient temperature;

DOI:10.1055/s-1988-27760

upstream raw materials:

2,2'-Anhydro-1-(3'-O-methylsulfonyl-β-D-arabinofuranosyl)thymine

2,2'-Anhydro-1-(5'-O-Benzoyl-3'-O-methylsulfonyl-β-D-arabinofuranosyl)thymine

5'-O-(4,4'-dimethoxytrityl)-1-(2,3-anhydro-β-D-lyxofuranosyl)thymine

1-(3',5'-di-O-benzoyl-2'-deoxy-2'-iodo-β-D-xylopentofuranosyl)thymine

Downstream raw materials:

3'-cyano-3'-deoxy-β-D-arabinofuranosylthymine