N6-Phenoxyacetyladenosine

Base Information

• Chemical Name: N6-Phenoxyacetyladenosine
• CAS No.: 119824-65-6
• Molecular Formula: C18H19N5O6
• Molecular Weight: 401.37300
• Mol file: 119824-65-6.mol

Synonyms:N6-(phenoxyacetyl)adenosine;N6-phenoxyacetyladenosine;

Chemical Property of N6-Phenoxyacetyladenosine

Chemical Property:

• PSA: 151.85000
• LogP: -0.47170

Purity/Quality:

97% ^*data from raw suppliers

N-(9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)-2-phenoxyacetamide 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N6-Phenoxyacetyladenosine

There total 19 articles about 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: 81.0%

3-methyl-1-(phenoxyacetyl)-1H-imidazol-3-ium chloride + adenosine (58-61-7) → N6-phenoxyacetyladenosine (119824-65-6)

Guidance literature:

adenosine; With pyridine; chloro-trimethyl-silane; at 20 ℃; for 2h;

3-methyl-1-(phenoxyacetyl)-1H-imidazol-3-ium chloride; With pyridine; In dichloromethane; at 4 - 20 ℃; for 18.5h;

DOI:10.1002/hlca.201000403

Reference yield:

2-phenoxyacetic acid (122-59-8) + adenosine (58-61-7) → N6-phenoxyacetyladenosine (119824-65-6)

Guidance literature:

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

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

DOI:10.1016/j.bmcl.2005.07.078

Reference yield:

adenosine (58-61-7) → N6-phenoxyacetyladenosine (119824-65-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 0 deg C -> r.t. for 1-2 h

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

With ethanol; water; In pyridine;

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

upstream raw materials:

O^2'_,O3'_,O5'-tris-trimethylsilanyl-adenosine

Phenoxyacetyl chloride

adenosine

1-(phenoxyacetyl)-1H-imidazole

Downstream raw materials:

5'-O-dimethoxytrityl-N₆-phenoxyacetyladenosine

N-(9-{(2R,3R,4S,5R)-3,4-Dihydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-9H-purin-6-yl)-2-phenoxy-acetamide

2',3'-O-methoxymethylidene-N⁶-phenoxyacetyladenosine

N⁶-phenoxyacetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)adenosine

Refernces

• 1、 Takahashi, Mayumi,Grajkowski, Andrzej,Cawrse, Brian M.,Beaucage, Serge L.. "Innovative 2′- O-Imino-2-propanoate-Protecting Group for Effective Solid-Phase Synthesis and 2′- O-Deprotection of RNA Sequences". . p. 4944 - 4956. Retrieved 2021.
• 2、 Tripathi, Snehlata,Misra, Krishna,Sanghvi, Yogesh S.. "Polymer supported carbodiimide strategy for the synthesis of N-acylated derivatives of deoxy- and ribo purinenucleosides using active esters". . p. 5045 - 5048. Retrieved 2007/10/03.