2-IODO-5'-ETHYLCARBOXAMIDO-2',3'-O-ISOPROPYLIDINEADENOSINE

Base Information

• Chemical Name: 2-IODO-5'-ETHYLCARBOXAMIDO-2',3'-O-ISOPROPYLIDINEADENOSINE
• CAS No.: 162936-24-5
• Molecular Formula: C15H19IN6O4
• Molecular Weight: 474.25363
• Mol file: 162936-24-5.mol

Synonyms:2-IODO-5'-ETHYLCARBOXAMIDO-2',3'-O-ISOPROPYLIDINEADENOSINE;1-(6-AMino-2-iodo-9H-purin-9-yl)-1-deoxy-N-ethyl-2,3-O-(1-Methylethylidene)-β-D-ribofuranuronaMide;2-IODO-5'-ETHYLCARBOXAMIDO-2',3'-O-ISOPROPYLIDENEADENOSINE

Chemical Property of 2-IODO-5'-ETHYLCARBOXAMIDO-2',3'-O-ISOPROPYLIDINEADENOSINE

Chemical Property:

• Melting Point: 204-206°C
• PSA: 126.41000
• LogP: 1.53880
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

2-Iodo-5’-ethylcarboxamido-2’,3’-O-isopropylidineadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Iodo-5’-ethylcarboxamido-2’,3’-O-isopropylidineadenosine (cas# 162936-24-5) is a compound useful in organic synthesis.

Technology Process of 2-IODO-5'-ETHYLCARBOXAMIDO-2',3'-O-ISOPROPYLIDINEADENOSINE

There total 3 articles about 2-IODO-5'-ETHYLCARBOXAMIDO-2',3'-O-ISOPROPYLIDINEADENOSINE 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: 96.0%

C21H21IN8O5 (1195939-23-1) → N-ethyl-1'-deoxy-1'-(6-amino-2-iodo-9H-purin-9-yl)-2',3'-O-isopropylidene-β-D-ribofuranuronamide (162936-24-5)

Guidance literature:

With ammonia; In water; acetonitrile; at 25 ℃; for 3h;

DOI:10.1016/j.tet.2009.08.057

Reference yield: 71.0%

ethylamine (75-04-7,85404-22-4) + (3aS,4S,6R,6aR)-6-(6-amino-2-iodo-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid (141018-26-0) → N-ethyl-1'-deoxy-1'-(6-amino-2-iodo-9H-purin-9-yl)-2',3'-O-isopropylidene-β-D-ribofuranuronamide (162936-24-5)

Guidance literature:

(3aS,4S,6R,6aR)-6-(6-amino-2-iodo-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid; With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In ethanol; dichloromethane; at 20 ℃; for 24h;

ethylamine; In ethanol; dichloromethane; at 20 ℃; for 24h;

Reference yield:

ethylamine (75-04-7,85404-22-4) + (3aS,4S,6R,6aR)-6-(6-Amino-2-iodo-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl chloride → N-ethyl-1'-deoxy-1'-(6-amino-2-iodo-9H-purin-9-yl)-2',3'-O-isopropylidene-β-D-ribofuranuronamide (162936-24-5)

Guidance literature:

In dichloromethane; for 1h; Yield given; Ambient temperature;

DOI:10.1021/jm00009a007

upstream raw materials:

ethylamine

(3aS,4S,6R,6aR)-6-(6-amino-2-iodo-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid

C₂₁H₂₁IN₈O₅

Downstream raw materials:

(3aS,4S,6R,6aR)-6-[6-Amino-2-(3-hydroxy-3-phenyl-prop-1-ynyl)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide

2-iodo-5'-N-ethylcarboxamidoadenosine

2-(5-phenyl)pentyn-1-yl-5'-N-ethylcarboxamidoadenosine

(3aS,4S,6R,6aR)-6-{6-[3-(3-Chloro-phenyl)-ureido]-2-iodo-purin-9-yl}-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide

Refernces

• 1、 Hong, Yang,Bonacorsi Jr., Samuel J.,Tian, Yuan,Gong, Sharon,Zhang, Donglu,Humphreys, W. Griffith,Balasubramanian, Balu,Cheesman, Edward H.,Zhang, Zhiqin,Castner, James F.,Crane, Paul D.. "Synthesis of [1,2-3H]ethylamine hydrochloride and [ 3H]-labeled apadenoson for a human ADME study". . p. 113 - 117. Retrieved 2008/09/18.
• 2、 Cristalli, Gloria,Camaioni, Emidio,Vittori, Sauro,Volpini, Rosaria,Borea, Pier Andrea,et al.. "2-Aralkynyl and 2-Heteroalkynyl Derivatives of Adenosine-5'-N-ethyluronamide as Selective A2a Adenosine Receptor Agonists". . p. 1462 - 1472. Retrieved 2007/10/02.