Nucleoside Q

Base Information

• Chemical Name: Nucleoside Q
• CAS No.: 57072-36-3
• Molecular Formula: C17H23N5O7
• Molecular Weight: 409.39
• Mol file: 57072-36-3.mol

Synonyms:Q (nucleoside);Queuosine;

Chemical Property of Nucleoside Q

Chemical Property:

• Vapor Pressure: 3.39E-28mmHg at 25°C
• Refractive Index: 1.864
• Boiling Point: 816.5°C at 760 mmHg
• PKA: 12.52±0.70(Predicted)
• Flash Point: 447.6°C
• PSA: 199.11000
• Density: 2g/cm³
• LogP: -2.35980

Purity/Quality:

97% ^*data from raw suppliers

NucleosideQ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Nucleoside Q is a is a modified 7-deazaguanosine nucleoside located in the anticodon wobble position of four amino acid-specific tRNAs. In bacteria, Nucleoside Q is produced from GTP (G837905) via the 7-deazaguanosine (D201390) precursor. Nucleoside Q and its derivatives usually replace guanosine in the anticodon of tRNAsGUN of eubacteria as well as cytoplasmic and mitochondrial tRNAs of some eukaryotes.

Technology Process of Nucleoside Q

There total 7 articles about Nucleoside Q 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%

2-amino-3,4-dihydro-5-<(3S,4R,5S)-4,5-dihydroxy-4,5-O-isopropylidenecyclopent-1-en-3-ylaminomethyl>-3-methoxymethyl-7-(2,3-O-isopropylidene-β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-4-one (66242-47-5,71050-03-8,71050-04-9) → 2-amino-3,4-dihydro-5-<(3S,4R,5S)-4,5-dihydroxycyclopent-1-en-3-ylaminomethyl>-7-β-D-ribofuranosyl-7H-pyrrolo<2,3-d>pyrimidin-4-one (57072-36-3)

Guidance literature:

In hydrogenchloride; at 80 ℃; for 8h;

DOI:10.1016/S0040-4020(01)87419-6

Reference yield:

C20H27N5O7 → 2-amino-3,4-dihydro-5-<(3S,4R,5S)-4,5-dihydroxycyclopent-1-en-3-ylaminomethyl>-7-β-D-ribofuranosyl-7H-pyrrolo<2,3-d>pyrimidin-4-one (57072-36-3)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 5h;

DOI:10.1002/anie.200604579

Reference yield:

6-bromo-2-diacetylamino-3,4-dihydro-5-hydroxymethyl-3-methoxymethyl-7-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-4-one (87875-07-8) → 2-amino-3,4-dihydro-5-<(3S,4R,5S)-4,5-dihydroxycyclopent-1-en-3-ylaminomethyl>-7-β-D-ribofuranosyl-7H-pyrrolo<2,3-d>pyrimidin-4-one (57072-36-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / AcOK, H₂ / 10percent Pd/C / methanol; H₂O / 0.5 h / Ambient temperature

2: 1.) MnO₂ / 1.) acetonitrile, r.t., 3 h; 2.) 28percent aq. NH₄OH-MeOH, r.t., 15 h

3: 2.) NaBH₄ / 1.) benzene, r.t., 5 h; 2.) EtOH, 0 deg C, 1 h

4: 89 percent / aq. HCl / 8 h / 80 °C

With manganese(IV) oxide; sodium tetrahydroborate; hydrogen; potassium acetate; palladium on activated charcoal; In hydrogenchloride; methanol; water;

DOI:10.1016/S0040-4020(01)87419-6

upstream raw materials:

2-amino-3,4-dihydro-5-<(3S,4R,5S)-4,5-dihydroxy-4,5-O-isopropylidenecyclopent-1-en-3-ylaminomethyl>-3-methoxymethyl-7-(2,3-O-isopropylidene-β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-4-one

6-bromo-2-diacetylamino-3,4-dihydro-5-hydroxymethyl-3-methoxymethyl-7-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-4-one

2-amino-3,4-dihydro-5-formyl-3-methoxymethyl-7-(2,3-O-isopropylidene-β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-4-one

2-diacetylamino-3,4-dihydro-5-hydroxymethyl-3-methoxymethyl-7-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-4-one