5'-Deoxy-5'-aminoadenosine

Base Information

• Chemical Name: 5'-Deoxy-5'-aminoadenosine
• CAS No.: 14365-44-7
• Molecular Formula: C₁₀H₁₄N₆O₃
• Molecular Weight: 266.26
• NSC Number: 103561,238990
• DSSTox Substance ID: DTXSID50931976
• Mol file: 14365-44-7.mol

Synonyms:5'-amino-5'-deoxyadenosine;5'-deoxy-5'-aminoadenosine

Chemical Property of 5'-Deoxy-5'-aminoadenosine

Chemical Property:

• Boiling Point: 647.6 °C at 760 mmHg
• Flash Point: 345.4 °C
• PSA: 145.33000
• Density: 2.08 g/cm³
• LogP: -0.73210
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 266.11273833
• Heavy Atom Count: 19
• Complexity: 334

Purity/Quality:

99%, ^*data from raw suppliers

5''-Amino-5''-deoxyadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CN)O)O)N
• Uses: 5''-Amino-5''-deoxyadenosine is an adenosine kinase inhibitor.

Technology Process of 5'-Deoxy-5'-aminoadenosine

There total 14 articles about 5'-Deoxy-5'-aminoadenosine 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%

5'-azido-5'-deoxyadenosine (737-76-8) → 5'-amino-5'-deoxyadenosine (14365-44-7,30589-93-6,34340-04-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In N,N-dimethyl acetamide; benzene; Heating;

DOI:10.1016/0040-4039(91)80150-5

Reference yield: 75.0%

2-[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-isoindole-1,3-dione (220579-81-7) → 5'-amino-5'-deoxyadenosine (14365-44-7,30589-93-6,34340-04-0)

Guidance literature:

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

Reference yield:

5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine (21950-36-7) → 5'-amino-5'-deoxyadenosine (14365-44-7,30589-93-6,34340-04-0)

Guidance literature:

With formic acid; for 24h; Ambient temperature;

DOI:10.1021/jm00347a014

upstream raw materials:

5'-azido-5'-deoxyadenosine

5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine

N⁶-benzoyl-5'-azidoadenosine

5'-azido-5'-deoxy-N⁶-benzoyl-2',3'-O-isopropylidene adenosine

Downstream raw materials:

N-benzyloxycarbonyl-N'-(2',3'-O-isopropylidene-5'-deoxyadenosin-5'-yl)sulfamide

(6-{[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-carbamoyl}-hexyl)-carbamic acid benzyl ester

(5-{[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-carbamoyl}-pentyl)-carbamic acid benzyl ester

(4-{[(2R,3S,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl]-carbamoyl}-butyl)-carbamic acid benzyl ester

Refernces

• 1、 -. "5'-Deoxidation-5'-isopropyl-substituted-amino nucleoside compound and preparing method and application thereof". . . Retrieved 2019/05/28.
• 2、 Wang, Ting,Lee, Hyun Joo,Tosh, Dilip K.,Kim, Hea Ok,Pal, Shantanu,Choi, Sun,Lee, Yoonji,Moon, Hyung Ryong,Zhao, Long Xuan,Lee, Kang Man,Jeong, Lak Shin. "Design, synthesis, and molecular modeling studies of 5′-deoxy-5′-ureidoadenosine: 5′-ureido group as multiple hydrogen bonding donor in the active site of S-adenosylhomocysteine hydrolase". . p. 4456 - 4459. Retrieved 2008/02/10.