Queuine

Base Information

• Chemical Name: Queuine
• CAS No.: 86496-18-6
• Molecular Formula: C₁₂H₁₅N₅O₃*2ClH
• Molecular Weight: 350.205
• Mol file: 86496-18-6.mol

Synonyms:Queuine Dihydrochloride

Chemical Property of Queuine

Chemical Property:

• PSA: 141.04000
• LogP: -0.68350

Purity/Quality:

96% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: It is one of the modified base which is found at first anticodon position of specific tRNAs.

Technology Process of Queuine

There total 13 articles about Queuine 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: 95.0%

2-amino-5({[(3a′R,4′S,6a′S)-2,2-dimethyl-4,6a′-dihydro-3a′H-cyclopenta[d][1,3]dioxol-4-yl]amino}methyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one monohydrochloride (1412403-11-2) → queuine dihydrochloride (86496-18-6)

Guidance literature:

With hydrogenchloride; In methanol; water; for 5h; Inert atmosphere; Reflux;

DOI:10.1039/c2ob26387d

Reference yield: 91.0%

5-({[(3′aR,4′S,6′aS)-4′,6′a-dihydro-3′aH-spiro[cyclohexane-1,2′-cyclopenta[d][1,3]dioxole]-4′-yl]amino}methyl)-2-amino-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-4-one monohydrochloride (1412403-12-3) → queuine dihydrochloride (86496-18-6)

Guidance literature:

With hydrogenchloride; In methanol; water; for 5h; Inert atmosphere; Reflux;

DOI:10.1039/c2ob26387d

Reference yield:

(R,S)-2-[2-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-3-nitropropyl]-1H-isoindole-1,3(2H)-dione → queuine dihydrochloride (86496-18-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / water / 0.08 h / 20 °C / Inert atmosphere

1.2: -5 - 20 °C / Inert atmosphere

2.1: hydrogenchloride / water / 6 h / Inert atmosphere; Reflux

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere

3.2: 5 h / 50 - 65 °C / Inert atmosphere

4.1: hydrogenchloride / water; methanol / 5 h / Inert atmosphere; Reflux

With hydrogenchloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium hydroxide; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1039/c2ob26387d

upstream raw materials:

(3a′S,4′S,6a′S)-4′,6a′-dihydro-3a′H-spiro[cyclohexane-1,2′-cyclopenta[d][1,3]dioxol]-4′-yl 4-nitrobenzoate

(3aR,4S,6aS)-2,2-dimethyl-2H,3aH,4H,6aH-cyclopenta[d][1,3]-dioxol-4-ol

(3′aR,4′S,6′aS)-4′,6′a-dihydro-3′aH-spiro[cyclohexane-1,2′-cyclopenta[d][1,3]dioxole]-4′-ol

(3aS,4R,6aS)-4-bromo-2,2-dimethyl-2H,3aH,4H,6aH-cyclopenta-[d][1,3]dioxole

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