5'-Amino-5'-deoxy-2',3'-O-(1-methylethylidene)-adenosine

Base Information

• Chemical Name: 5'-Amino-5'-deoxy-2',3'-O-(1-methylethylidene)-adenosine
• CAS No.: 21950-36-7
• Molecular Formula: C13H18N6O3
• Molecular Weight: 306.324
• DSSTox Substance ID: DTXSID20461750
• Nikkaji Number: J652.648I
• Wikidata: Q72435581
• Mol file: 21950-36-7.mol

Synonyms:21950-36-7;5'-Amino-5'-deoxy-2',3'-O-(1-methylethylidene)-adenosine;9-((3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine;9-[(3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-amine;Adenosine, 5'-amino-5'-deoxy-2',3'-O-(1-methylethylidene)-;9-[(3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-amine;SCHEMBL460251;DTXSID20461750;RGJLVQRLOVOJRF-WOUKDFQISA-N;9-((3aR,4S,6R,6aR)-6-(Aminomethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine;CS-D1218;MFCD15833219;AKOS016005359;DS-4004;5'-Amino-5'-O-(1-methylethylidene)-adenosine;A848692;5'-Amino-5'-deoxy-2',3'-O-isopropylidineadenosine;5'-Amino-5'-deoxy-2' pound not3'-O-(1-methylethylidene)-adenosine;9-((3 aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine;9-((3aR,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine

Chemical Property of 5'-Amino-5'-deoxy-2',3'-O-(1-methylethylidene)-adenosine

Chemical Property:

• Melting Point: 202-203℃
• Boiling Point: 553.1±60.0 °C(Predicted)
• PKA: 9.08±0.29(Predicted)
• PSA: 123.33000
• Density: 1.80±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 1.06620
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 306.14403846
• Heavy Atom Count: 22
• Complexity: 438

Purity/Quality:

99% ^*data from raw suppliers

5''-Amino-5’-deoxy-2’,3’-O-(1-methylethylidene)adenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OC2C(OC(C2O1)N3C=NC4=C(N=CN=C43)N)CN)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H](O[C@H]([C@@H]2O1)N3C=NC4=C(N=CN=C43)N)CN)C
• Use Description: Adenosine, 5'-amino-5'-deoxy-2',3'-O-(1-methylethylidene)-, is a chemical compound with applications in various fields. In the field of pharmaceuticals and drug development, it can serve as a structural analog of adenosine, a naturally occurring nucleoside with important physiological roles. Its modified structure makes it useful for studying adenosine receptor activity and designing novel adenosine-based medications for conditions like cardiac arrhythmias, asthma, and certain neurological disorders. Additionally, in biochemistry and molecular biology, it may find use as a tool for studying nucleoside metabolism and nucleic acid chemistry. Its significance varies within these fields, but it consistently plays a pivotal role in advancing our understanding of adenosine-related pathways and in potentially developing therapeutic agents for various medical conditions.

Technology Process of 5'-Amino-5'-deoxy-2',3'-O-(1-methylethylidene)-adenosine

There total 21 articles about 5'-Amino-5'-deoxy-2',3'-O-(1-methylethylidene)-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%

5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine (34245-48-2) → 5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine (21950-36-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol;

DOI:10.1039/c4ob01734j

Reference yield: 96.4%

2-[[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl]-2,3-dihydro-1H-isoindol-1,3-dione (80860-44-2) → 5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine (21950-36-7)

Guidance literature:

With hydrazine hydrate; In ethanol; for 2h; Heating;

DOI:10.1016/S0040-4020(98)01004-7

Reference yield: 76.0%

2',3'-isopropylidene adenosine (362-75-4) → 5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine (21950-36-7)

Guidance literature:

With phthalimide; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 14h;

upstream raw materials:

5'-azido-5'-deoxy-2',3'-O-isopropylideneadenosine N¹-oxide

2-[[(3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl]-2,3-dihydro-1H-isoindol-1,3-dione

5'-azido-5'-deoxy-2',3'-O-isopropylidene adenosine

((3aR,4R,6R,6aR)-6-(6-benzamido-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate

Downstream raw materials:

1-(5'-deoxy-2',3'-O-isopropylidene adenosin-5'-yl)-2-methyl-3-phenylsulfonylisothiourea

4-nitro-phenol

Pentanedioic acid [(3aR,4R,6R,6aR)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-amide (1-oxo-2,3-dihydro-1H-isoindol-4-yl)-amide

Refernces

• 1、 Tamura, Tomoki,Nakano, Shun,Nakata, Eiji,Morii, Takashi. "Construction of a library of structurally diverse ribonucleopeptides with catalytic groups". . p. 1 - 7. Retrieved 2017.
• 2、 Liu, Qing,Cai, Xiaoqing,Yang, Dehua,Chen, Yi,Wang, Yafang,Shao, Liming,Wang, Ming-Wei. "Cycloalkane analogues of sinefungin as EHMT1/2 inhibitors". . p. 4579 - 4594. Retrieved 2017.
• 3、 Bobi?eva, Olga,Bobrovs, Raitis,Ka?epe, Iveta,Patetko, Liene,Kalni??, Gints,?i?ovs, Mihails,Bula, Anna L.,Grī Nberga, Solveiga,Borodu??is, Mā Rti??,Ramata-Stunda, Anna,Rostoks, Nils,Jirgensons, Aigars,Tā Rs, Kaspars,Jaudzems, Kristaps. "Potent SARS-CoV-2 mRNA Cap Methyltransferase Inhibitors by Bioisosteric Replacement of Methionine in SAM Cosubstrate". supporting information. p. 1102 - 1107. Retrieved 2021/06/30.
• 4、 Galan, M. Carmen,Ghirardello, Mattia,Ledru, Helene,Sau, Abhijit. "Chemo-selective Rh-catalysed hydrogenation of azides into amines". supporting information. . Retrieved 2020/02/18.