2'-Deoxy-8,5'-cycloadenosine

Base Information

• Chemical Name: 2'-Deoxy-8,5'-cycloadenosine
• CAS No.: 117182-88-4
• Molecular Formula: C10H11 N5 O3
• Molecular Weight: 249.229
• DSSTox Substance ID: DTXSID60922315
• Nikkaji Number: J991.462E
• Mol file: 117182-88-4.mol

Synonyms:2'-deoxy-8,5'-cycloadenosine;5',8-cyclo-2'-deoxyadenosine;8,5'-CDA;8,5'-cyclo-2'-deoxyadenosine

Chemical Property of 2'-Deoxy-8,5'-cycloadenosine

Chemical Property:

• Boiling Point: 721.2°Cat760mmHg
• PKA: 12.12±0.40(Predicted)
• Flash Point: 390°C
• PSA: 119.31000
• Density: 2.43g/cm³
• LogP: -0.31490
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 249.08618923
• Heavy Atom Count: 18
• Complexity: 358

Purity/Quality:

97% ^*data from raw suppliers

8,5'(S)-CYCLO-2'-DEOXYADENOSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2C(C3=NC4=C(N=CN=C4N3C1O2)N)O)O
• Isomeric SMILES: C1[C@@H]([C@H]2[C@H](C3=NC4=C(N=CN=C4N3[C@@H]1O2)N)O)O

Technology Process of 2'-Deoxy-8,5'-cycloadenosine

There total 8 articles about 2'-Deoxy-8,5'-cycloadenosine 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:

calf thymus DNA, γ-irradiated → 8-oxo-7,8-dihydro-2'-deoxyguanosine (31077-24-4,62471-63-0) + (5'S)-5',8-cyclo-2'-deoxyguanosine (105929-27-9) + 2'-Deoxyguanosine (961-07-9) + 7,8-dihydro-8-oxo-2'-deoxyguanosine (88847-89-6) + (5'S)-5',8-cyclo-2'-deoxyadenosine (117182-88-4) + (5'R)-5',8-cyclo-2'-deoxyadenosine + (5'R)-5',8-cyclo-2'-deoxyguanosine + 2'-Deoxycytidine (951-77-9) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) + 2'-deoxy-D-adenosine (958-09-8,7005-15-4)

Guidance literature:

calf thymus DNA, γ-irradiated; With DNase II; Penicillium citrium nuclease P₁; phosphodiesterase II; 9-erythro-(2-hydroxy-3-n-nonyl)adenine hydrochloride; at 37 ℃; for 2h; pH=6; aq. buffer; Enzymatic reaction;

With phosphodiesterase I from Crotalus adamentus venom; alkaline phosphatase; at 37 ℃; for 2h; pH=8; aq. buffer; Enzymatic reaction;

With DNase II; Penicillium citrium nuclease P₁; phosphodiesterase II; at 37 ℃; for 2h; pH=6; optical yield given as %de; aq. buffer; Enzymatic reaction;

DOI:10.1039/c004531d

Reference yield:

dA(pdA)19 → 2-deoxyinosine (890-38-0) + N6-hydroxy-2'-deoxyadenosine (51385-49-0) + 8-oxo-7,8-dihydro-2'-deoxyguanosine (31077-24-4,62471-63-0) + 2'-Deoxyadenosine N1-oxide (3506-01-2) + 2’-deoxyisoguanosine (106449-56-3) + C10H11N5O4 + C10H11N5O3 + C10H15N5O4 + C19H26N10O8 + C19H26N10O7 + C10H15N5O4 + C10H15N5O4 + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) + N-[4-Amino-6-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-pyrimidin-5-yl]-formamide + (5'S)-5',8-cyclo-2'-deoxyadenosine (117182-88-4) + (5'R)-5',8-cyclo-2'-deoxyadenosine + 5',8-cyclo-2',5'-dideoxyadenosine

Guidance literature:

With dihydrogen peroxide; iron(III); NADH; In ethanol; Reagent/catalyst;

DOI:10.1080/07391102.2012.682206

Reference yield:

2'-deoxy-D-adenosine (958-09-8,7005-15-4) → 2-deoxyinosine (890-38-0) + N6-hydroxy-2'-deoxyadenosine (51385-49-0) + 8-oxo-7,8-dihydro-2'-deoxyguanosine (31077-24-4,62471-63-0) + 2'-Deoxyadenosine N1-oxide (3506-01-2) + 2’-deoxyisoguanosine (106449-56-3) + C10H11N5O4 + C10H11N5O3 + C10H15N5O4 + C19H26N10O8 + C19H26N10O7 + C10H15N5O4 + C10H15N5O4 + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) + N-[4-Amino-6-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-ylamino)-pyrimidin-5-yl]-formamide + (5'S)-5',8-cyclo-2'-deoxyadenosine (117182-88-4) + (5'R)-5',8-cyclo-2'-deoxyadenosine + 5',8-cyclo-2',5'-dideoxyadenosine

Guidance literature:

With dihydrogen peroxide; iron(II); In ethanol;

DOI:10.1080/07391102.2012.682206

upstream raw materials:

8-bromo-2'-deoxyadenosine

2'-deoxy-D-adenosine

2'-deoxyadenosine 3'-monophosphate

2'-deoxyadenosine-5'-monophosphoric acid

Refernces

• 1、 Chatgilialoglu, Chryssostomos,Guerra, Maurizio,Mulazzani, Quinto G.. "Model studies of DNA C5′ radicals. Selective generation and reactivity of 2′-deoxyadenosin-5′-yl radical". . p. 3839 - 3848. Retrieved 2003.
• 2、 Navacchia, Maria Luisa,Chatsilialoglu, Chryssostomos,Montevecchi, Pier Carlo. "C5′-adenosinyl radical cyclization. A stereochemical investigation". . p. 4445 - 4452. Retrieved 2007/10/03.