3,4-di-O-benzyl-6-O-levulinoyl-[13C₆]-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 3,4-di-O-benzyl-6-O-levulinoyl-[13C₆]-D-arabino-hex-1-enitol
• CAS No.: 697746-80-8
• Molecular Formula: C₂₅H₂₈O₆
• Molecular Weight: 430.428
• Mol file: 697746-80-8.mol

Synonyms:3,4-di-O-benzyl-6-O-levulinoyl-[13C₆]-D-arabino-hex-1-enitol

Chemical Property of 3,4-di-O-benzyl-6-O-levulinoyl-[13C₆]-D-arabino-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-di-O-benzyl-6-O-levulinoyl-[13C₆]-D-arabino-hex-1-enitol

There total 5 articles about 3,4-di-O-benzyl-6-O-levulinoyl-[13C₆]-D-arabino-hex-1-enitol 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: 99.0%

levulinic acid (123-76-2) + 3,4-di-O-benzyl-[13C6]-D-arabino-hex-1-enitol (697746-79-5) → 3,4-di-O-benzyl-6-O-levulinoyl-[13C6]-D-arabino-hex-1-enitol (697746-80-8)

Guidance literature:

With dmap; bis-(diisopropylphenyl)carbodiimidol; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1002/mrc.1364

Reference yield:

3,4,6-tri-O-acetyl-D-(U-13C)glucal (153362-93-7,478529-35-0,478529-37-2,478529-36-1) → 3,4-di-O-benzyl-6-O-levulinoyl-[13C6]-D-arabino-hex-1-enitol (697746-80-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: MeONa / methanol / 2 h / 20 °C

1.2: 89 percent / imidazole / dimethylformamide / 2 h / 0 °C

2.1: 95 percent / NaH / dimethylformamide / 2 h / 0 °C

3.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C

4.1: 99 percent / DMAP; bis-(diisopropylphenyl)carbodiimidol / CH₂Cl₂ / 2 h / 0 °C

With dmap; bis-(diisopropylphenyl)carbodiimidol; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/mrc.1364

Reference yield:

[glucose-U-(13)C6]-1,2,3,4,6-penta-O-acetyl-α/β-D-glucopyranose (299172-50-2) → 3,4-di-O-benzyl-6-O-levulinoyl-[13C6]-D-arabino-hex-1-enitol (697746-80-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: HBr; AcOH / CH₂Cl₂ / 6 h / 0 - 20 °C

1.2: 1474 mg / Zn; CuSO₄*5H₂O; AcOH / AcONa / H₂O; ethyl acetate / 2 h / 0 - 20 °C

2.1: MeONa / methanol / 2 h / 20 °C

2.2: 89 percent / imidazole / dimethylformamide / 2 h / 0 °C

3.1: 95 percent / NaH / dimethylformamide / 2 h / 0 °C

4.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C

5.1: 99 percent / DMAP; bis-(diisopropylphenyl)carbodiimidol / CH₂Cl₂ / 2 h / 0 °C

With dmap; bis-(diisopropylphenyl)carbodiimidol; tetrabutyl ammonium fluoride; hydrogen bromide; sodium methylate; sodium hydride; acetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/mrc.1364

upstream raw materials:

levulinic acid

3,4-di-O-benzyl-[13C₆]-D-arabino-hex-1-enitol

3,4,6-tri-O-acetyl-D-(U-¹³C)glucal

[glucose-U-(13)C6]-1,2,3,4,6-penta-O-acetyl-α/β-D-glucopyranose

Downstream raw materials:

dibutyl 3,4-di-O-benzyl-6-O-levulinoyl-2-O-pivaloyl-[13C₆]-D-glucopyranosyl phosphate