diethyl (3R,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate

Base Information

• Chemical Name: diethyl (3R,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate
• CAS No.: 948832-20-0
• Molecular Formula: C₁₆H₂₆NO₅P
• Molecular Weight: 343.36

Synonyms:diethyl (3R,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate

Chemical Property of diethyl (3R,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate

Chemical Property:

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Technology Process of diethyl (3R,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate

There total 6 articles about diethyl (3R,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate 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: 88.0%

diethyl (3R,5R)-5-(acetoxymethyl)-2-[(S)-1-phenylethyl]izoxazolidinyl-3-phosphonate (948832-22-2) → diethyl (3R,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate (948832-20-0)

Guidance literature:

With ammonium hydroxide; In ethanol; at 20 ℃; for 4h;

DOI:10.1016/j.tetasy.2007.06.006

Reference yield: 23.0%

N-[(S)-1-phenylethyl]-C-(diethoxyphosphoryl)nitrone (948832-15-3) + allyl alcohol (107-18-6) → diethyl (3R,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate (948832-20-0) + diethyl (3S,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate (948832-16-4) + diethyl (3R,5S)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate + diethyl (3S,5S)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate (948832-17-5)

Guidance literature:

In toluene; at 60 ℃; for 48h;

DOI:10.1016/j.tetasy.2007.06.006

Reference yield:

N-((1S)-1-phenylethyl)hydroxylamine (53933-47-4) → diethyl (3R,5R)-5-(hydroxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate (948832-20-0)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 48 h / 60 °C

In toluene;

DOI:10.1016/j.tetasy.2007.06.006

upstream raw materials:

diethyl (3R,5R)-5-(acetoxymethyl)-2-[(S)-1-phenylethyl]izoxazolidinyl-3-phosphonate

N-[(S)-1-phenylethyl]-C-(diethoxyphosphoryl)nitrone

allyl alcohol

N-((1S)-1-phenylethyl)hydroxylamine

Downstream raw materials:

diethyl (3R,5R)-5-(mesyloxymethyl)-2-[(S)-1-phenylethyl]isoxazolidinyl-3-phosphonate

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