2'-Deoxy-N6-phenoxyacetyladenosine

Base Information

• Chemical Name: 2'-Deoxy-N6-phenoxyacetyladenosine
• CAS No.: 110522-74-2
• Molecular Formula: C18H19 N5 O5
• Molecular Weight: 385.379
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID50441262
• Nikkaji Number: J2.049.507C
• Wikidata: Q82257960
• Mol file: 110522-74-2.mol

Synonyms:110522-74-2;2'-Deoxy-N6-phenoxyacetyladenosine;N6-Pheac-deoxyadenosine;N-(9-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)-2-phenoxyacetamide;N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]-2-phenoxyacetamide;n6-phenoxyacetyldeoxyadenosine;6-n-phenoxyacetyldeoxyadenosine;SCHEMBL7035979;DTXSID50441262;HWSKJANFAKYDDL-GZBFAFLISA-N;2/'-Deoxy-N6-phenoxyacetyladenosine;N-(Phenoxyacetyl)-2'-deoxyadenosine;AC-32159;F13430;A855510;J-700289;N-{9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-yl}-2-phenoxyacetamide

Chemical Property of 2'-Deoxy-N6-phenoxyacetyladenosine

Chemical Property:

• PKA: 7.87±0.43(Predicted)
• PSA: 131.62000
• Density: 1.58±0.1 g/cm3(Predicted)
• LogP: 0.55750
• Storage Temp.: Store at 0°C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 385.13861872
• Heavy Atom Count: 28
• Complexity: 535

Purity/Quality:

98%, ^*data from raw suppliers

N-(9-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)-2-phenoxyacetamide 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=NC3=C(N=CN=C32)NC(=O)COC4=CC=CC=C4)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)NC(=O)COC4=CC=CC=C4)CO)O

Technology Process of 2'-Deoxy-N6-phenoxyacetyladenosine

There total 6 articles about 2'-Deoxy-N6-phenoxyacetyladenosine 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:

2-phenoxyacetic acid (122-59-8) + 2'-deoxy-D-adenosine (958-09-8,7005-15-4) → N6-(phenoxyacetyl)-2'-deoxyadenosine (110522-74-2)

Guidance literature:

2-phenoxyacetic acid; With pyridine; 4-nitro-phenol; dicyclohexyl-carbodiimide; TEA; In 1,4-dioxane; at 20 ℃; for 2h;

2'-deoxy-D-adenosine; With pyridine; dicyclohexyl-carbodiimide; In 1,4-dioxane; at 0 ℃; for 2h;

DOI:10.1016/j.bmcl.2005.07.078

Reference yield:

2-phenoxyacetic acid (122-59-8) → N6-(phenoxyacetyl)-2'-deoxyadenosine (110522-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / Ambient temperature; 30-60 min

2: 2.) EtOH, H₂O / 1.) pyridine, acetonitrile, overnight, r.t.; 2.) 0 deg C

With ethanol; water; In acetonitrile;

DOI:10.1016/0040-4039(95)02011-D

Reference yield:

Phenoxyacetyl chloride (701-99-5) + 2'-deoxy-D-adenosine (958-09-8,7005-15-4) → N6-(phenoxyacetyl)-2'-deoxyadenosine (110522-74-2)

Guidance literature:

With sodium hydroxide; Yield given. Multistep reaction; 1.) pyridine, 3 h, room temperature, 2.) pyridine-EtOH, 10 min, 0 deg C;

upstream raw materials:

Phenoxy-acetic acid (2R,3S,5R)-2-(2-phenoxy-acetoxymethyl)-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester

Phenoxyacetyl chloride

2'-deoxy-D-adenosine

9-((2R,4S,5R)-4-Trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamine

Downstream raw materials:

Phosphoric acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester; compound with triethyl-amine

N⁶-phenoxyacetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine

Carbonic acid (2R,3S,5R)-3-hydroxy-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester

2'-deoxy-D-adenosine

Refernces

• 1、 Pirrung, Michael C.,Fallon, Lara,McGall, Glenn. "Proofing of Photolithographic DNA Synthesis with 3′,5′-Dimethoxybenzoinyloxycarbonyl-Protected Deoxynucleoside Phosphoramidites". . p. 241 - 246. Retrieved 2007/10/03.
• 2、 Singh, Ramendra K.,Misra, K.. "Improvements in Oligodeoxyribonucleotide Synthesis using Phenoxyacetyl as Amino Protecting Group". . p. 409 - 417. Retrieved 2007/10/02.