7-thia-8-oxoguanosine

Base Information

• Chemical Name: 7-thia-8-oxoguanosine
• CAS No.: 122970-40-5
• Molecular Formula: C₁₀H₁₂N₄O₆S
• Molecular Weight: 316.294
• Mol file: 122970-40-5.mol

Synonyms:7-Thia-8-oxoguanosine;ANA 245; ICN 10146; Immunosine; Immusine; Isatoribine; N 10146; NARI 10146;TOG; TOG (ligand)

Chemical Property of 7-thia-8-oxoguanosine

Chemical Property:

• Vapor Pressure: 2.64E-18mmHg at 25°C
• Boiling Point: 626.2°Cat760mmHg
• PKA: 6.80±0.20(Predicted)
• Flash Point: 332.5°C
• PSA: 191.93000
• Density: 2.38g/cm³
• LogP: -2.07880

Purity/Quality:

97% ^*data from raw suppliers

Isatoribine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Immunomodulator (regulates cell growth by perturbing signal transduction). Isatoribine is a novel guanosine analogue showing immunostimulatory activity both in vivo and in vitro.

Technology Process of 7-thia-8-oxoguanosine

There total 5 articles about 7-thia-8-oxoguanosine 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: 78.0%

5-amino-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)thiazolo<4,5-d>pyrimidine-2,7(3H,6H)-dione (122970-39-2) → 7-thia-8-oxoguanosine (122970-40-5)

Guidance literature:

With sodium methylate; In methanol; for 16h; Ambient temperature;

DOI:10.1021/jm00163a064

Reference yield:

5-aminothiazolo<4,5-d>pyrimidine-2,7(3H,6H)-dione (30161-97-8) → 7-thia-8-oxoguanosine (122970-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) HMDS, (NH₄)2SO₄, 2.) trimethylsilyl trifluoromethanesulfonate / 1.) pyridine, reflux, 4 h, 2.) acetonitrile, RT, 16 h

2: 78 percent / NaOCH₃ / methanol / 16 h / Ambient temperature

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; sodium methylate; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol;

DOI:10.1021/jm00163a064

Reference yield:

1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (14215-97-5) → 7-thia-8-oxoguanosine (122970-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) HMDS, (NH₄)2SO₄, 2.) trimethylsilyl trifluoromethanesulfonate / 1.) pyridine, reflux, 4 h, 2.) acetonitrile, RT, 16 h

2: 78 percent / NaOCH₃ / methanol / 16 h / Ambient temperature

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; sodium methylate; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol;

DOI:10.1021/jm00163a064

upstream raw materials:

5-amino-3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)thiazolo<4,5-d>pyrimidine-2,7(3H,6H)-dione

5-aminothiazolo<4,5-d>pyrimidine-2,7(3H,6H)-dione

1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose

Downstream raw materials:

5-Amino-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)thiazolo[4,5-d]-pyrimidine-2,7(3H,6H)-dione

5-acetylamino-7-(2,4,6-triisopropyl-benzenesulfonyloxy)-3-(2,3,5-tri-O-acetyl-3-βD-ribofuranosyl)thiazolo[4,5-d]pyrimidin-2-one

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