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

Base Information

• Chemical Name: dibutyl 3,4-di-O-benzyl-6-O-levulinoyl-2-O-pivaloyl-[13C₆]-D-glucopyranosyl phosphate
• CAS No.: 697746-81-9
• Molecular Formula: C₃₈H₅₅O₁₂P
• Molecular Weight: 740.755

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

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

Chemical Property:

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

There total 7 articles about dibutyl 3,4-di-O-benzyl-6-O-levulinoyl-2-O-pivaloyl-[13C₆]-D-glucopyranosyl phosphate 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: 72.0%

3,3-dimethyldioxirane (74087-85-7) + pivaloyl chloride (3282-30-2) + dibutyl phosphate (107-66-4) + 3,4-di-O-benzyl-6-O-levulinoyl-[13C6]-D-arabino-hex-1-enitol (697746-80-8) → dibutyl 3,4-di-O-benzyl-6-O-levulinoyl-2-O-pivaloyl-[13C6]-D-glucopyranosyl phosphate (697746-81-9)

Guidance literature:

3,3-dimethyldioxirane; 3,4-di-O-benzyl-6-O-levulinoyl-[13C₆]-D-arabino-hex-1-enitol; In dichloromethane; acetone; at 0 ℃; for 0.333333h;

dibutyl phosphate; In dichloromethane; at -78 - 0 ℃;

pivaloyl chloride; With dmap; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/mrc.1364

Reference yield:

levulinic acid (123-76-2) → dibutyl 3,4-di-O-benzyl-6-O-levulinoyl-2-O-pivaloyl-[13C6]-D-glucopyranosyl phosphate (697746-81-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / DMAP; bis-(diisopropylphenyl)carbodiimidol / CH₂Cl₂ / 2 h / 0 °C

2.1: CH₂Cl₂; acetone / 0.33 h / 0 °C

2.2: CH₂Cl₂ / -78 - 0 °C

2.3: 72 percent / DMAP / CH₂Cl₂ / 0 - 20 °C

With dmap; bis-(diisopropylphenyl)carbodiimidol; In dichloromethane; acetone;

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) → dibutyl 3,4-di-O-benzyl-6-O-levulinoyl-2-O-pivaloyl-[13C6]-D-glucopyranosyl phosphate (697746-81-9)

Guidance literature:

Multi-step reaction with 5 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

5.1: CH₂Cl₂; acetone / 0.33 h / 0 °C

5.2: CH₂Cl₂ / -78 - 0 °C

5.3: 72 percent / DMAP / CH₂Cl₂ / 0 - 20 °C

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

DOI:10.1002/mrc.1364

upstream raw materials:

3,3-dimethyldioxirane

pivaloyl chloride

dibutyl phosphate

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

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