2'-Deoxysangivamycin

Base Information

• Chemical Name: 2'-Deoxysangivamycin
• CAS No.: 83379-28-6
• Molecular Formula: C12H15N5O4
• Molecular Weight: 293.2786
• DSSTox Substance ID: DTXSID20232306
• Nikkaji Number: J372.999K
• Wikidata: Q83113322
• ChEMBL ID: CHEMBL3142730
• Mol file: 83379-28-6.mol

Synonyms:2'-deoxysangivamycin;4-amino-7-(2-deoxy-beta-D-ribofuranosyl)pyrrolo(2,3-d)pyrimidine-5-carboxamide

Chemical Property of 2'-Deoxysangivamycin

Chemical Property:

• Vapor Pressure: 1.59E-24mmHg at 25°C
• Boiling Point: 763.7°Cat760mmHg
• Flash Point: 415.7°C
• PSA: 149.51000
• Density: 1.92g/cm³
• LogP: 0.03460
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 293.11240398
• Heavy Atom Count: 21
• Complexity: 411

Purity/Quality:

97% ^*data from raw suppliers

2'-DEOXYSANGIVAMYCIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C3=C(N=CN=C32)N)C(=O)N)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C3=C(N=CN=C32)N)C(=O)N)CO)O
• General Description: 2'-Deoxysangivamycin is a nucleoside antibiotic structurally related to adenosine, known for its significant antitumor properties. It is synthesized via a stereospecific sodium salt glycosylation procedure, which efficiently produces β-anomer nucleosides, including 2'-deoxysangivamycin, as part of a broader effort to develop potential chemotherapeutic agents.

Technology Process of 2'-Deoxysangivamycin

There total 15 articles about 2'-Deoxysangivamycin 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: 94.0%

4-amino-5-cyano-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (15676-19-4) → 4-amino-5-carboxamido-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (83379-28-6)

Guidance literature:

With water;

DOI:10.1021/ja00350a052

Reference yield: 63.0%

4-amino-6-bromo-7-(2-deoxy-β-D-erythro-pentofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carboxamide (110089-49-1) → 4-amino-5-carboxamido-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (83379-28-6)

Guidance literature:

With ammonium hydroxide; hydrogen; palladium on activated charcoal; In ethanol; water; for 24h; under 2068.6 Torr;

DOI:10.1016/S0040-4020(01)96068-5

Reference yield:

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-carboxamido-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine (83379-28-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / TBAF / toluene; tetrahydrofuran / 2 h / 80 °C

2: 94 percent / H₂O

With tetrabutyl ammonium fluoride; water; In tetrahydrofuran; toluene;

DOI:10.1021/ja00350a052

upstream raw materials:

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

4-amino-6-bromo-7-(2-deoxy-β-D-erythro-pentofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carboxamide

6,2'-S-cyclosangivamycin hydrobromide

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

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.

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