[ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)adenine

Base Information

• Chemical Name: [ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)adenine
• CAS No.: 503173-77-1
• Molecular Formula: C₂₆H₂₃N₅O₇
• Molecular Weight: 522.443
• Mol file: 503173-77-1.mol

Synonyms:[ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)adenine

Chemical Property of [ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)adenine

There total 5 articles about [ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)adenine 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: 68.0%

N-benzoyladenine (4005-49-6) + 13C5-1′, 2 ′-di-O-acetyl-3 ′ ,5 ′-di-O-benzoyl-β-D-ribofuranose (503173-75-9) → [ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)adenine (503173-77-1)

Guidance literature:

N-benzoyladenine; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; Heating;

¹³C₅-1′, 2 ′-di-O-acetyl-3 ′ ,5 ′-di-O-benzoyl-β-D-ribofuranose; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 3.5h; Heating;

DOI:10.1016/S0040-4020(02)01246-2

Reference yield:

<1,2,3,4,5,6-13C6>-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (126590-65-6) → [ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)adenine (503173-77-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 94 percent / pyridinium dichromate; acetic anhydride / CH₂Cl₂ / 1.5 h / Heating

2.1: H₅IO₆ / ethyl acetate / 2 h / 20 °C

2.2: 80 percent / NaBH₄ / ethanol / 0.5 h

3.1: 95 percent / pyridine / 3 h / 20 °C

4.1: 87 percent / H₂SO₄; AcOH / 20 °C

5.1: HMDS; (NH₄)2SO₄ / Heating

5.2: 68 percent / TMSOTf / CH₂Cl₂ / 3.5 h / Heating

With pyridine; ammonium sulfate; dipyridinium dichromate; sulfuric acid; acetic anhydride; acetic acid; periodic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; ethyl acetate;

DOI:10.1016/S0040-4020(02)01246-2

Reference yield:

[glu-13C6]-1,2:5,6-di-O-isopropylidene-3-oxo-α-D-glucofuranose (503173-73-7) → [ribose-13C5]-1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-ribofuranosyl)adenine (503173-77-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: H₅IO₆ / ethyl acetate / 2 h / 20 °C

1.2: 80 percent / NaBH₄ / ethanol / 0.5 h

2.1: 95 percent / pyridine / 3 h / 20 °C

3.1: 87 percent / H₂SO₄; AcOH / 20 °C

4.1: HMDS; (NH₄)2SO₄ / Heating

4.2: 68 percent / TMSOTf / CH₂Cl₂ / 3.5 h / Heating

With pyridine; ammonium sulfate; sulfuric acid; acetic acid; periodic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In ethyl acetate;

DOI:10.1016/S0040-4020(02)01246-2

upstream raw materials:

N-benzoyladenine

¹³C₅-1′, 2 ′-di-O-acetyl-3 ′ ,5 ′-di-O-benzoyl-β-D-ribofuranose

<1,2,3,4,5,6-13C6>-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

<1,2,3,4,5-13C5>-1,2-O-isopropylidene-α-D-ribofuranose

Downstream raw materials:

[1′,2′,3′,4′,5′-¹³C₅] adenosine