3'-Deoxysangivamycin

Base Information

• Chemical Name: 3'-Deoxysangivamycin
• CAS No.: 83379-31-1
• Molecular Formula: C12H15N5O4
• Molecular Weight: 293.2786
• Nikkaji Number: J373.000J
• Mol file: 83379-31-1.mol

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

Chemical Property of 3'-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: -2
• 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

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(C1O)N2C=C(C3=C(N=CN=C32)N)C(=O)N)CO
• Isomeric SMILES: C1[C@H](O[C@H]([C@@H]1O)N2C=C(C3=C(N=CN=C32)N)C(=O)N)CO

Technology Process of 3'-Deoxysangivamycin

There total 7 articles about 3'-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: 90.0%

3'-deoxytoyocamycin (105582-76-1) → 3'-Deoxysangivamycin (83379-31-1)

Guidance literature:

With Dowex 1X₂(OH^-); In water; Ambient temperature;

DOI:10.1021/jm00386a007

Reference yield: 49.0%

4-amino-7-<2-O-acetyl-3-deoxy-3-iodo-5-O-(2,5,5-trimethyl-4-oxo-1,3-dioxolan-2-yl)-β-D-xylofuranosyl>pyrrolo<2,3-d>pyrimidine-5-carboxamide (83379-29-7) → 3'-Deoxysangivamycin (83379-31-1)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In ethanol; water; for 18h; under 2068.6 Torr;

DOI:10.1021/jm00355a006

Reference yield:

2-Acetoxy-2-methyl-propionic acid (2R,3R,4S,5R)-5-(4-amino-5-cyano-pyrrolo[2,3-d]pyrimidin-7-yl)-3-bromo-4-hydroxy-tetrahydro-furan-2-ylmethyl ester (105582-78-3) → 3'-Deoxysangivamycin (83379-31-1) + 3'-deoxytoyocamycin (105582-76-1)

Guidance literature:

With ammonia; hydrogen; triethylamine; palladium on activated charcoal; Yield given. Multistep reaction. Yields of byproduct given; 1.) EtOH, RT, 48 h, 2.) MeOH, RT, 36 h;

DOI:10.1021/jm00386a007

upstream raw materials:

4-amino-7-<2-O-acetyl-3-deoxy-3-iodo-5-O-(2,5,5-trimethyl-4-oxo-1,3-dioxolan-2-yl)-β-D-xylofuranosyl>pyrrolo<2,3-d>pyrimidine-5-carboxamide

3'-deoxytoyocamycin

2-Acetoxy-2-methyl-propionic acid (2R,3R,4S,5R)-5-(4-amino-5-cyano-pyrrolo[2,3-d]pyrimidin-7-yl)-3-bromo-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

Vengicide

Refernces

• 1、 Clercq, Erik De,Balzarini, Jan,Madej, Danuta,Hansske, Fritz,Robins, Morris J.. "Nucleic Acid Related Compounds. 51. Synthesis and Biological Properties of Sugar-Modified Analogues of the Nucleoside Antibiotics Tubercidin, Toyocamycin, Sangivamycin, and Formycin". . p. 481 - 486. Retrieved 2007/10/02.