2'-Deoxypseudouridine

Base Information

• Chemical Name: 2'-Deoxypseudouridine
• CAS No.: 39967-60-7
• Molecular Formula: C₉H₁₂N₂O₅
• Molecular Weight: 228.205
• DSSTox Substance ID: DTXSID00440386
• Nikkaji Number: J483.866A
• Wikidata: Q82256680
• Mol file: 39967-60-7.mol

Synonyms:2'-Deoxypseudouridine;Deoxypseudouridine;39967-60-7;5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidine-2,4-dione;SCHEMBL658719;DTXSID00440386;2,4(1H,3H)-Pyrimidinedione,5-(2-deoxy-b-D-erythro-pentofuranosyl)-;NSC804517;AKOS040740767;CS-7717;NSC-804517;MS-23290;PD102954;HY-101970;5-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione;5-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

Chemical Property of 2'-Deoxypseudouridine

Chemical Property:

• Melting Point: 220-222 °C(Solv: ethanol (64-17-5); methanol (67-56-1))
• PKA: 8.52±0.10(Predicted)
• PSA: 115.41000
• Density: 1.503±0.06 g/cm3(Predicted)
• LogP: -1.75360
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 228.07462149
• Heavy Atom Count: 16
• Complexity: 354

Purity/Quality:

97% ^*data from raw suppliers

2'-Deoxypseudouridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1C2=CNC(=O)NC2=O)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1C2=CNC(=O)NC2=O)CO)O
• Uses: 2'-Deoxypseudouridine is a useful research chemical compound.

Technology Process of 2'-Deoxypseudouridine

There total 23 articles about 2'-Deoxypseudouridine 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: 92.0%

2',3'-dideoxy-3'-oxopseudouridine (142189-87-5) → 2'-Deoxypseudouridine (39967-60-7)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In acetonitrile; at 0 ℃; for 3h; stereoselective reaction;

DOI:10.1039/c9nj01012b

Reference yield: 89.0%

2'-deoxy-3',5'-O-(tetraisopropyldisiloxanyl)pseudouridine (80545-51-3) → 2'-Deoxypseudouridine (39967-60-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/jo00342a022

Reference yield: 12.3%

pseudouridine (1445-07-4) → 3'-Deoxy-ψ-uridine (69265-05-0) + 2'-Deoxypseudouridine (39967-60-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 2-acetoxy-2-methylpropanoyl chloride; Yield given. Multistep reaction; 1.) acetonitrile, 2 h, reflux, 2.) 1,2-dimethoxyethane, 48 h, reflux;

DOI:10.1021/jo00331a005

upstream raw materials:

pseudouridine

O³,O⁵-dibenzyl-D-erythro-2-deoxy-pentose

5-lithio-2,4-di-t-butoxypyrimidine

2'-deoxy-3',5'-O-(tetraisopropyldisiloxanyl)pseudouridine

Downstream raw materials:

5-(α-D-erythro-2-deoxy-pentofuranosyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione

1,3-Dimethyl-2'-deoxypseudouridine

Pseudothymidine

3'-deoxy-1,3-dimethyl-ψ-uridine

Refernces

• 1、 Yu, Cheng-Ping,Chang, Hsin-Yun,Chien, Tun-Cheng. "Total synthesis of pseudouridine: Via Heck-type C-glycosylation". . p. 8796 - 8803. Retrieved 2019/06/14.
• 2、 Zhang,Daves Jr.. "Syntheses of 2'-deoxypseudouridine, 2'-deoxyformycin B, and 2',3'-dideoxyformycin B by palladium-mediated glycal-aglycon coupling". . p. 4690 - 4696. Retrieved 2007/10/02.