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

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

• 1、 Ramasamy,Robins,Revankar. "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". . p. 5869 - 5878. Retrieved 2007/10/02.
• 2、 Maruyama,Wotring,Townsend. "Pyrrolopyrimidine nucleosides. 18. Synthesis and chemotherapeutic activity of 4-amino-7-(3-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carboxamide(3'-deoxysangivamycin) and 4-amino-7-(2-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carboxamide". . p. 25 - 29. Retrieved 2007/10/02.