1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methylpyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methylpyrimidine-2,4-dione
• CAS No.: 16710-13-7
• Molecular Formula: C10H14 N2 O6
• Molecular Weight: 258.231
• NSC Number: 112513
• DSSTox Substance ID: DTXSID10937277
• Mol file: 16710-13-7.mol

Synonyms:1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methylpyrimidine-2,4-dione;1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methylpyrimidine-2,4-dione;SCHEMBL13423825;DTXSID10937277;NSC112513;NSC-112513;4-Hydroxy-6-methyl-1-pentofuranosylpyrimidin-2(1H)-one

Chemical Property of 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methylpyrimidine-2,4-dione

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 124.78000
• Density: 1.576g/cm³
• LogP: -2.54350
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 258.08518617
• Heavy Atom Count: 18
• Complexity: 409

Purity/Quality:

97% ^*data from raw suppliers

6-Methyluridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)NC(=O)N1C2C(C(C(O2)CO)O)O
• Uses: 6-Methyluridine exhibited weak antimalarial activity against P. falciparum 3D7 isolate. It is a weak substrate of Escherichia coli pyrimidine nucleoside phosphorylase.

Technology Process of 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methylpyrimidine-2,4-dione

There total 30 articles about 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-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: 89.0%

2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl)-6-methyluridine (142682-83-5) → 6-methyluridine (16710-13-7)

Guidance literature:

With water; trifluoroacetic acid; at 0 - 20 ℃; for 1h;

DOI:10.1021/jo400364p

Reference yield: 86.0%

2',3'-O-isopropylidene-6-methyluridine (72055-46-0) → 6-methyluridine (16710-13-7)

Guidance literature:

With formic acid; for 1h; Ambient temperature;

DOI:10.1055/s-1982-29767

Reference yield: 67.0%

1β-D-ribofuranosyl-3-benzyl-6-methyluracil (25691-86-5) → 6-methyluridine (16710-13-7)

Guidance literature:

With boron tribromide; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jm950675q

upstream raw materials:

2',3'-O-isopropylidene-6-methyluridine

tert-butyl peroxyacetate

uridine

6-methyl-cytidine

Downstream raw materials:

5'-O-4,4'-dimethoxytrityl-6-methyluridine

6-Methyluracil

D-ribose

5'-O-4,4'-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-6-methyluridine

Refernces

• 1、 Jones, Simon S.,Reese, Colin B.,Ubasawa, Aiko. "A Convenient Synthesis of 5-Methyluridine from Uridine". . p. 259 - 260. Retrieved 1982.
• 2、 Shih, Yu-Chiao,Yang, Ya-Ying,Lin, Chun-Chi,Chien, Tun-Cheng. "Synthesis of 6-alkyluridines from 6-cyanouridine via zinc(II) chloride-catalyzed nucleophilic substitution with alkyl grignard reagents". . p. 4027 - 4036. Retrieved 2013/06/04.