81691-10-3

Basic information

• Product Name: 2'-deoxy-3-methylpseudouridine
• Synonyms: 2'-deoxy-3-methylpseudouridine
• CAS NO: 81691-10-3
• Molecular Formula: C10H14 N2 O5
• Molecular Weight: 242.23
• Mol File: 81691-10-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.452g/cm³
• Refractive Index: 1.584
• CAS DataBase Reference: 2'-deoxy-3-methylpseudouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-deoxy-3-methylpseudouridine(81691-10-3)
• EPA Substance Registry System: 2'-deoxy-3-methylpseudouridine(81691-10-3)

Safety Data

• Hazardous Substances Data: 81691-10-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H14N2O5/c1-12-9(15)5(3-11-10(12)16)7-2-6(14)8(4-13)17-7/h3,6-8,13-14H,2,4H2,1H3,(H,11,16)/t6-,7-,8+/m0/s1

Upstream product

• 81691-08-9 3-methyl-3',5'-O-tetraisopropyldisiloxanyl-2'-O-<(imidazol-1-yl)thiocarbonyl>-ψ-uridine 
• 81691-05-6 1-Acetyl-5-((2S,3S,4R,5R)-3,4-bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-3-methyl-1H-pyrimidine-2,4-dione 
• 81691-04-5 1-acetyl-2',3',5'-tri-O-trimethylsilyl-ψ-uridine 
• 81691-07-8 3-methyl-3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)pseudouridine 
• 81691-06-7 3-methylpseudouridine 
• 81691-09-0 2'-deoxy-3-methyl-3',5'-O-tetraisopropyldisiloxanyl-ψ-uridine 

Relevant articles and documents

Synthesis of 3-methylpseudouridine and 2'-deoxy-3-methyl-pseudouridine.

The first chemical synthesis of 3-methyl-psi-uridine (5) and its 2'-deoxy analogue (9) has been achieved. psi-Uridine was trimethylsilylated and the crude product was treated with acetyl chloride, to give the 1-acetyl derivative (3). Crude 3 was methylated with dimethoxymethyldimethylamine and then saponified, to give crystalline 5 in 82% overall yield. Treatment of 5 with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane afforded the 3'5'-protected product, which was converted into the 2'O-[(imidazol-1-yl) thiocarbonyl] derivative 7. Reduction of 7 with tributyltin hydride followed by deblocking of the product gave crystalline 2'-deoxy-3-methyl-psi-uridine (9) in 35% yield form 5.