2',3'-O-(Isopropylidene)uridine 5'-acetate

Base Information

• Chemical Name: 2',3'-O-(Isopropylidene)uridine 5'-acetate
• CAS No.: 15922-23-3
• Molecular Formula: C14H18 N2 O7
• Molecular Weight: 326.306
• European Community (EC) Number: 240-061-2
• DSSTox Substance ID: DTXSID40936076
• Nikkaji Number: J219.903C
• Wikidata: Q82912220
• Mol file: 15922-23-3.mol

Synonyms:15922-23-3;2',3'-O-(Isopropylidene)uridine 5'-acetate;EINECS 240-061-2;AI3-63056;5'-O-acetyl-2',3'-O-isopropylideneuridine;DTXSID40936076;[(3aR,4R,6R,6aR)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl acetate;2'-O,3'-O-Isopropylidene-5'-O-acetyluridine;2/',3/'-O-(Isopropylidene)uridine 5/'-acetate;Uridine, 2',3'-O-(1-methylethylidene)-, 5'-acetate;1-[5-O-Acetyl-2,3-O-(1-methylethylidene)pentofuranosyl]-4-hydroxypyrimidin-2(1H)-one

Chemical Property of 2',3'-O-(Isopropylidene)uridine 5'-acetate

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 9.25±0.10(Predicted)
• Flash Point: °C
• PSA: 109.11000
• Density: 1.328g/cm³
• LogP: -0.07050
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 326.11140092
• Heavy Atom Count: 23
• Complexity: 574

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C2C(C(O1)N3C=CC(=O)NC3=O)OC(O2)(C)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@@H]2[C@H]([C@@H](O1)N3C=CC(=O)NC3=O)OC(O2)(C)C

Technology Process of 2',3'-O-(Isopropylidene)uridine 5'-acetate

There total 3 articles about 2',3'-O-(Isopropylidene)uridine 5'-acetate 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: 100.0%

2',3'-O-isopropylideneuridine (362-43-6) + acetic anhydride (108-24-7) → 1-(5-O-Acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)uracil (15922-23-3)

Guidance literature:

With triethylamine; In dichloromethane; for 0.0833333h; Ambient temperature;

DOI:10.1021/ja00197a047

Reference yield: 35.0%

5'-O-acetyl-2',3'-O-isopropylidene-5'-phenylselenouridine → 1-(5-O-Acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)uracil (15922-23-3) + (6S,5'R)-5'-O-acetyl-5,6-dihydro-2'3'-O-isopropylidene-6,5'-cyclouridine + (6S,5'S)-5'-O-acetyl-5,6-dihydro-2'3'-O-isopropylidene-6,5'-cyclouridine

Guidance literature:

With tri-n-butyl-tin hydride; bis(tri-n-butyltin); In benzene; Yields of byproduct given; Ambient temperature; Irradiation;

DOI:10.1016/0040-4039(94)88369-6

Reference yield:

→ 1-(5-O-Acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)uracil (15922-23-3)

Guidance literature:

2',3'-O-Isopropylidenuridin, Acetanhyrid;

DOI:10.1007/BF00471583

upstream raw materials:

2',3'-O-isopropylideneuridine

acetic anhydride

Downstream raw materials:

2',3'-O-isopropylideneuridine

β-D-arabinofuranosylisocytosine

O^5'-acetyl-O^2'-(toluene-4-sulfonyl)-uridine

uridine 2'-monophosphate

Refernces

• 1、 Kolobushkina et al.. "". . . Retrieved 1973.
• 2、 Ritter, Anne,Egli, Daniel,Bernet, Bruno,Vasella, Andrea. "Oligonucleotide analogues with integrated bases and backbone Part 17 1. Conformational analysis and association of ethylene-, oxymethylene-, and thiomethylene-linked self-complementary adenosine and uridine dimers". scheme or table. p. 673 - 714. Retrieved 2009/02/07.