3'-Amino-3'-deoxyadenosine

Base Information

• Chemical Name: 3'-Amino-3'-deoxyadenosine
• CAS No.: 2504-55-4
• Molecular Formula: C₁₀H₁₄N₆O₃
• Molecular Weight: 266.26
• Hs Code.: 2934999090
• Nikkaji Number: J80.507F
• Pharos Ligand ID: QMYRRGV4QG3S
• ChEMBL ID: CHEMBL338352
• Mol file: 2504-55-4.mol

Synonyms:3'-amino-3'-deoxyadenosine;3'-deoxy-3'-aminoadenosine

Chemical Property of 3'-Amino-3'-deoxyadenosine

Chemical Property:

• Melting Point: 260-261 °C
• Refractive Index: 1.7000 (estimate)
• Boiling Point: 657.6°Cat760mmHg
• PKA: 13.27±0.70(Predicted)
• Flash Point: 351.5°C
• PSA: 145.33000
• Density: 2.08g/cm³
• LogP: -0.73210
• 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

3'-Amino-3'-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)CO)N)O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)N)O)N

Technology Process of 3'-Amino-3'-deoxyadenosine

There total 38 articles about 3'-Amino-3'-deoxyadenosine 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: 98.0%

9-[3-(benzylamino)-3-deoxy-β-D-ribofuranosyl]adenine (67313-10-4,134934-82-0) → 3'-amino-3'-deoxyadenosine (2504-55-4,26315-51-5,32077-67-1,51014-76-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; Ambient temperature; further catalyst and solvent;

DOI:10.1016/S0040-4039(01)80390-7

Reference yield: 97.0%

3'-Azido-3'-deoxyadenosine (58699-62-0) → 3'-amino-3'-deoxyadenosine (2504-55-4,26315-51-5,32077-67-1,51014-76-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 6h; under 760 Torr;

DOI:10.1016/S0040-4020(98)00819-9

Reference yield: 85.2%

9-(3'-amino-3'-deoxy-2',3',5'-triacetyl-D-ribofuranosyl)-N6-benzoyladenine → 3'-amino-3'-deoxyadenosine (2504-55-4,26315-51-5,32077-67-1,51014-76-7)

Guidance literature:

With sodium methylate; In methanol; for 15h; Heating;

DOI:10.3987/COM-94-6992

upstream raw materials:

3'-phthalimido-3'-deoxy-adenosine

N⁶,O^2'_,O5'-tribenzoyl-3'-phthalimido-3'-deoxy-adenosine

puromycin E

9-[3-(benzylamino)-3-deoxy-β-D-ribofuranosyl]adenine

Downstream raw materials:

3'-Amino-3'-desoxyinosin

[5-(1-{1-[5-(6-amino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-ylcarbamoyl]-5-benzyloxycarbonylamino-pentylcarbamoyl}-5-benzyloxycarbonylamino-pentylcarbamoyl)-5-tert-butoxycarbonylamino-pentyl]-carbamic acid benzyl ester

3'-(N-tert-butyloxycarbonyl-L-phenylalanyl-amido)-3'-deoxyadenosine

Refernces

• 1、 Pal, Chandan,Velusamy, Arventh,Sunkari, Yashoda Krishna,Chakraborty, Tushar Kanti. "Studies on sugar puckering and glycosidic stabilities of 3′-amino-5′-carboxymethyl-3′,5′-dideoxy nucleoside mimics". supporting information. p. 6735 - 6740. Retrieved 2018/09/29.
• 2、 Takatsuki, Ken-Ichi,Yamamoto, Makoto,Ohgushi, Sumito,Kohmoto, Shigeo,Kishikawa, Keiki,Yamashita, Haruhiro. "A new protecting group '3′,5′-O-sulfinyl' for xylo-nucleosides. A simple and efficient synthesis of 3′-amino-3′-deoxyadenosine (a puromycin intermediate), 2,2′-anhydro-pyrimidine nucleosides and 2′,3′-anhydro-adenosine". . p. 137 - 140. Retrieved 2007/10/03.