2'3'-Isopropylidene-adenosine

Base Information

• Chemical Name: 2'3'-Isopropylidene-adenosine
• CAS No.: 362-75-4
• Molecular Formula: C13H17N5O4
• Molecular Weight: 307.309
• Hs Code.: 29349990
• European Community (EC) Number: 206-650-3
• Mol file: 362-75-4.mol

Synonyms:2',3'-isopropylideneadenosine;2',3'-O-isopropylidene adenosine

Chemical Property of 2'3'-Isopropylidene-adenosine

Chemical Property:

• Appearance/Colour: Crystalline
• Melting Point: 221-222 °C(lit.)
• Refractive Index: -105 ° (C=1, Dioxane)
• Boiling Point: 570.5 °C at 760 mmHg
• PKA: 14.14±0.10(Predicted)
• Flash Point: 298.8 °C
• PSA: 117.54000
• Density: 1.8 g/cm³
• LogP: 0.39950
• Storage Temp.: Store at RT.
• Solubility.: Dioxane (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 307.12805404
• Heavy Atom Count: 22
• Complexity: 439

Purity/Quality:

99% ^*data from raw suppliers

2’,3’-IsopropylideneAdenosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(OC2C(OC(C2O1)N3C=NC4=C(N=CN=C43)N)CO)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H](O[C@H](C2O1)N3C=NC4=C(N=CN=C43)N)CO)C
• Uses: 2',3'-O-Isopropylideneadenosine is used as an organic chemical synthesis intermediate.

Technology Process of 2'3'-Isopropylidene-adenosine

There total 49 articles about 2'3'-Isopropylidene-adenosine 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%

acetone (67-64-1) + adenosine (58-61-7) → 2',3'-isopropylidene adenosine (362-75-4)

Guidance literature:

With toluene-4-sulfonic acid; orthoformic acid triethyl ester; at 20 ℃;

DOI:10.1021/ml4002503

Reference yield: 100.0%

2,2-dimethoxy-propane (77-76-9) + acetone (67-64-1) + adenosine (58-61-7) → 2',3'-isopropylidene adenosine (362-75-4)

Guidance literature:

With toluene-4-sulfonic acid; at 20 ℃; for 72h; Inert atmosphere;

DOI:10.1021/acs.jnatprod.9b01231

Reference yield: 99.0%

2',3'-O-isopropylidene-6N-dibenzylaminomethylene adenosine → 2',3'-isopropylidene adenosine (362-75-4)

Guidance literature:

With hydrogen; palladium dihydroxide; In water; tert-butyl alcohol; under 3620.04 Torr; Ambient temperature;

DOI:10.1016/S0040-4039(97)10023-5

upstream raw materials:

acetone

adenosine

methanol

7,8-dihydro-2',3'-O-isopropylidene-N⁶,N⁶,7-tris(phenoxycarbonyl)-8,5'-O-cycloadenosine

Downstream raw materials:

O^2',O^3'-isopropylidene-[5']adenylic acid dibenzyl ester

5'-diphenylphosphate-5'-deoxy-2',3'-isopropylidene adenosine

2',3'-O-(1-methylethylidene)-adenosyl 5'-benzoate

5'-adenosine monophosphate

Refernces

• 1、 Zhang, Yixin,Pan, Yanbo,Yang, Wei,Liu, Wujun,Zou, Hanfa,Zhao, Zongbao K.. "Protein arginine allylation and subsequent fluorophore targeting". . p. 1438 - 1443. Retrieved 2013.
• 2、 Gadakh, Bharat,Smaers, Simon,Rozenski, Jef,Froeyen, Mathy,Van Aerschot, Arthur. "5'2-(N -aminoacyl)-sulfonamido-5'2-deoxyadenosine: Attempts for a stable alternative for aminoacyl-sulfamoyl adenosines as aaRS inhibitors". . p. 227 - 236. Retrieved 2015.
• 3、 Hernández-Vázquez, Eduardo,Chagoya, Victoria. "Potential utility of adenosine 5′-ester prodrugs to enhance its plasma half-life: Synthesis and molecular docking studies". . p. 2325 - 2335. Retrieved 2015.
• 4、 ?ileikyt?, Justina,Sundalam, Sunil,David, Larry L.,Cohen, Michael S.. "Chemical Proteomics Approach for Profiling the NAD Interactome". supporting information. p. 6787 - 6791. Retrieved 2021/05/29.
• 5、 Batta, Gyula,Bege, Miklós,Bereczki, Ilona,Borbás, Anikó,Debreczeni, Nóra,Herczeg, Mihály,Herczegh, Pál. "Tightly linked morpholino-nucleoside chimeras: new, compact cationic oligonucleotide analogues". supporting information. p. 8711 - 8721. Retrieved 2021/10/22.