4-amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Base Information

• Chemical Name: 4-amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• CAS No.: 15676-19-4
• Molecular Formula: C₁₂H₁₃N₅O₃
• Molecular Weight: 275.267
• Mol file: 15676-19-4.mol

Synonyms:2'-Deoxytoyocamycin

Chemical Property of 4-amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Chemical Property:

• Vapor Pressure: 3.95E-19mmHg at 25°C
• Boiling Point: 674.8°Cat760mmHg
• Flash Point: 361.9°C
• Density: 1.77g/cm³

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

There total 9 articles about 4-amino-7-(2-deoxy-beta-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 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: 89.0%

4-Amino-7-((2R,3aS,9aR)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (85335-81-5) → 4-amino-5-cyano-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (15676-19-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; toluene; at 80 ℃; for 2h;

DOI:10.1021/ja00350a052

Reference yield: 52.0%

copper(I) cyanide (544-92-3) + 7-deaza-2'-deoxy-7-iodoadenosine (166247-63-8,908130-61-0) → 4-amino-5-cyano-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (15676-19-4)

Guidance literature:

In pyridine; at 110 ℃; for 10h;

DOI:10.1080/07328319908044635

Reference yield: 41.0%

tri-n-butyltin cyanide (2179-92-2) + 7-deaza-2'-deoxy-7-iodoadenosine (166247-63-8,908130-61-0) → 4-amino-5-cyano-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (15676-19-4) + 2'-deoxy-7-deazaadenosine (60129-59-1)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 120 ℃; for 56h;

DOI:10.1080/07328319908044635

upstream raw materials:

4-amino-7-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carbonitrile

4-Amino-7-((2R,3aS,9aR)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

copper(I) cyanide

7-deaza-2'-deoxy-7-iodoadenosine

Downstream raw materials:

4-amino-5-carboxamido-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

5-cyano-7-[2-deoxy-5-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-4-{[(dimethylamino)-methylene]amino}-7H-pyrrolo[2,3-d]pyrimidine

Refernces

Total synthesis of 2'-deoxytoyocamycin, 2'-deoxysangivamycin and related 7-β-D-arabinofuranosylpyrrolo[2,3-d]pyrimidines via ring closure of pyrrole precursors prepared by the stereospecific sodium salt glycosylation procedure

10.1016/S0040-4020(01)96068-5

The research details the synthesis of nucleoside antibiotics with significant antitumor properties, specifically focusing on 2'-deoxytoyocamycin, 2'-deoxysangivamycin, and related compounds. The purpose of the study was to develop a stereospecific, high-yield glycosylation procedure to synthesize these nucleosides, which are structurally similar to adenosine and exhibit potent antitumor effects. The key chemicals used in the research include 2-bromo-(or ethylthio)-S-ethoxymethyleneemino-pyrrole-3,4-dicarbonitrile, 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose, and various other halosugars and heterocyclic compounds. The researchers employed a sodium salt glycosylation procedure, which allowed for the direct attachment of glycon moieties to fully aromatic pyrrole derivatives, resulting in the exclusive formation of β-anomer nucleosides. The synthesized compounds were characterized using various spectroscopic techniques, and the yields were reported for each step of the synthesis. The study concludes that this glycosylation procedure is a versatile and efficient method for synthesizing 2'-deoxyribofuranosyl and arabinofuranosyl nucleosides of the pyrrolo[2,3-d]pyrimidine ring system, providing a direct route for the synthesis of these potential chemotherapeutic agents.