(4R)-4-benzyl-3-[(2R,3S)-3,5,6-trihydroxy-2-methylhexanoyl]oxazolidin-2-one

Base Information

• Chemical Name: (4R)-4-benzyl-3-[(2R,3S)-3,5,6-trihydroxy-2-methylhexanoyl]oxazolidin-2-one
• CAS No.: 541513-57-9
• Molecular Formula: C₁₇H₂₃NO₆
• Molecular Weight: 337.373

Synonyms:(4R)-4-benzyl-3-[(2R,3S)-3,5,6-trihydroxy-2-methylhexanoyl]oxazolidin-2-one

Chemical Property of (4R)-4-benzyl-3-[(2R,3S)-3,5,6-trihydroxy-2-methylhexanoyl]oxazolidin-2-one

Chemical Property:

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Technology Process of (4R)-4-benzyl-3-[(2R,3S)-3,5,6-trihydroxy-2-methylhexanoyl]oxazolidin-2-one

There total 2 articles about (4R)-4-benzyl-3-[(2R,3S)-3,5,6-trihydroxy-2-methylhexanoyl]oxazolidin-2-one 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:

2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde (32233-44-6) + C21H32BNO3 → (4R)-4-benzyl-3-[(2R,3S)-3,5,6-trihydroxy-2-methylhexanoyl]oxazolidin-2-one (541513-57-9) + (4R)-4-benzyl-3-{(2R,3S)-4-[(1S)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-3-hydroxy-2-methylbutyryl}oxazolidin-2-one (541513-52-4)

Guidance literature:

2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde; C₂₁H₃₂BNO₃; In dichloromethane; at -65 - -5 ℃; for 1.66667h;

With dihydrogen peroxide; In methanol; dichloromethane; at 0 ℃; for 1h; Further stages.;

DOI:10.1039/b210606j

Reference yield:

(3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) → (4R)-4-benzyl-3-[(2R,3S)-3,5,6-trihydroxy-2-methylhexanoyl]oxazolidin-2-one (541513-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃N / CH₂Cl₂

2.1: CH₂Cl₂ / 1.67 h / -65 - -5 °C

2.2: 790 mg / aq. H₂O₂ / CH₂Cl₂; methanol / 1 h / 0 °C

With triethylamine; In dichloromethane;

DOI:10.1039/b210606j

Reference yield: 80.0%

acetone (67-64-1) + (4R)-4-benzyl-3-[(2R,3S)-3,5,6-trihydroxy-2-methylhexanoyl]oxazolidin-2-one (541513-57-9) → (4R)-4-benzyl-3-{(2R,3S)-4-[(1S)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-3-hydroxy-2-methylbutyryl}oxazolidin-2-one (541513-52-4)

Guidance literature:

With toluene-4-sulfonic acid; triethylamine; In ethyl acetate; at 20 ℃; for 2h;

DOI:10.1039/b210606j

upstream raw materials:

2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

(3R)-3-propionyl-4-benzyloxazolidin-2-one

Downstream raw materials:

(4R)-4-benzyl-3-{(2R,3S)-4-[(1S)-2,2-dimethyl-[1,3]-dioxolan-4-yl]-3-hydroxy-2-methylbutyryl}oxazolidin-2-one

(2R,3S,5S)-3,5-diacetoxy-6-bis(benzyloxy)phosphoryloxy-2-methylhexanoic acid benzyl ester

(2R,3S,5S)-6-bis(benzyloxy)phosphoryloxy-2-methyl-3,5-bis(tetrahydropyran-2-yloxy)hexanoic acid benzyl ester

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