Crotonoside

Base Information

• Chemical Name: Crotonoside
• CAS No.: 1818-71-9
• Molecular Formula: C10H13N5O5
• Molecular Weight: 283.244
• Hs Code.: 29349990
• UNII: 6V7FTE1Z1V
• Nikkaji Number: J14.939J
• Wikidata: Q27106249
• Metabolomics Workbench ID: 67805
• ChEMBL ID: CHEMBL1688963
• Mol file: 1818-71-9.mol

Synonyms:1,2-Dihydro-2-oxoadenosine;2'-deoxyisoguanosine;2-Hydroxyadenosine;crotonoside;isoguanosine

Chemical Property of Crotonoside

Chemical Property:

• Vapor Pressure: 2.83E-29mmHg at 25°C
• Melting Point: 237-241 °C(Solv: water (7732-18-5))
• Refractive Index: 1.955
• Boiling Point: 831oC at 760 mmHg
• PKA: 8.25±0.40(Predicted)
• Flash Point: 456.4oC
• PSA: 159.51000
• Density: 2.25 g/cm³
• LogP: -2.10550
• Storage Temp.: -20°C
• XLogP3: -3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 283.09166853
• Heavy Atom Count: 20
• Complexity: 544

Purity/Quality:

98% ^*data from raw suppliers

Crotonoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(NC(=O)N=C2N1C3C(C(C(O3)CO)O)O)N
• Isomeric SMILES: C1=NC2=C(NC(=O)N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N
• Uses: 2-?Hydroxyadenosine is an isoquinoline alkaloid displaying anticancer activity.

Technology Process of Crotonoside

There total 28 articles about Crotonoside 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: 95.0%

adenosine-2-amine (2096-10-8) → isoguanosine (1818-71-9)

Guidance literature:

With acetic acid; sodium nitrite; In water;

DOI:10.1021/acs.jmedchem.9b01611

Reference yield: 91.4%

adenosine-2-amine (2096-10-8) → 1,2-dihydro-2-oxoadenosine (1818-71-9)

Guidance literature:

With acetic acid; sodium nitrite; In water; at 50 ℃; for 0.0833333h;

DOI:10.1002/hlca.19980810502

Reference yield: 91.0%

N-<2-oxo-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-2,3-dihydropurin-6-yl>pyridinium chloride → isoguanosine (1818-71-9)

Guidance literature:

With ammonium hydroxide; at 50 ℃; for 5h;

upstream raw materials:

adenosine-2-amine

2',3'-O-Isopropylideneisoguanosine

2-iodoadenosine

2-hydroxy-6-amino-9-(2,3,5-tri-O-trimethylsilyl-β-D-ribofuranosyl)purine

Downstream raw materials:

6-(<(dimethylamino)methylidene>amino)-1,9-dihydro-9-(5'-O-(4-methoxytriphenylmethyl)-2'-O--β-D-ribofuranosyl)-2H-purin-2-one

6-(<(dimethylamino)methylidene>amino)-1,9-dihydro-9-(5'-O-(4-methoxytriphenylmethyl)-3'-O--β-D-ribofuranosyl)-2H-purin-2-one

6-(<(dimethylamino)methylidene>amino)-1,9-dihydro-9-<5'-O-(4-methoxytriphenylmethyl)-β-D-ribofuranosyl>-2H-purin-2-one

N'-(9-{(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-2-oxo-3,9-dihydro-2H-purin-6-yl)-N,N-dimethyl-formamidine

Refernces

• 1、 Swamy, B. E. Kumara,Venton, B. Jill. "Subsecond detection of physiological adenosine concentrations using fast-scan cyclic voltammetry". . p. 744 - 750. Retrieved 2007.
• 2、 Bhattarai, Sanjay,Pippel, Jan,Scaletti, Emma,Idris, Riham,Freundlieb, Marianne,Rolshoven, Georg,Renn, Christian,Lee, Sang-Yong,Abdelrahman, Aliaa,Zimmermann, Herbert,El-Tayeb, Ali,Müller, Christa E.,Str?ter, Norbert. "2-Substituted α,β-Methylene-ADP Derivatives: Potent Competitive Ecto-5′-nucleotidase (CD73) Inhibitors with Variable Binding Modes". supporting information. p. 2941 - 2957. Retrieved 2020/04/10.
• 3、 Bookser, Brett C.,Raffaele, Nicholas B.. "High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries". . p. 173 - 179. Retrieved 2007/10/03.