1-((2R,3R,4S,5S)-3,4-Dihydroxy-2-hydroxymethyl-5-phenyl-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone

Base Information

• Chemical Name: 1-((2R,3R,4S,5S)-3,4-Dihydroxy-2-hydroxymethyl-5-phenyl-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone
• CAS No.: 175480-85-0
• Molecular Formula: C₁₃H₁₄F₃NO₄
• Molecular Weight: 305.254

Synonyms:1-((2R,3R,4S,5S)-3,4-Dihydroxy-2-hydroxymethyl-5-phenyl-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone

Chemical Property of 1-((2R,3R,4S,5S)-3,4-Dihydroxy-2-hydroxymethyl-5-phenyl-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone

Chemical Property:

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Technology Process of 1-((2R,3R,4S,5S)-3,4-Dihydroxy-2-hydroxymethyl-5-phenyl-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone

There total 1 articles about 1-((2R,3R,4S,5S)-3,4-Dihydroxy-2-hydroxymethyl-5-phenyl-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone 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:

1,4-dideoxy-1,4-imino-1-(S)-phenyl-D-ribitol (151265-55-3) + trifluoroacetic anhydride (407-25-0) → 1-((2R,3R,4S,5S)-3,4-Dihydroxy-2-hydroxymethyl-5-phenyl-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone (175480-85-0)

Guidance literature:

With pyridine; ammonium hydroxide; Yield given. Multistep reaction; 2.) MeOH;

DOI:10.1021/ja9600385

Reference yield: 81.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 1-((2R,3R,4S,5S)-3,4-Dihydroxy-2-hydroxymethyl-5-phenyl-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone (175480-85-0) → 1-{(2R,3R,4S,5S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-5-phenyl-pyrrolidin-1-yl}-2,2,2-trifluoro-ethanone (175480-86-1)

Guidance literature:

With pyridine; dmap; triethylamine;

DOI:10.1021/ja9600385

Reference yield:

1-((2R,3R,4S,5S)-3,4-Dihydroxy-2-hydroxymethyl-5-phenyl-pyrrolidin-1-yl)-2,2,2-trifluoro-ethanone (175480-85-0) → 1-[(2R,3R,4S,5S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-5-phenyl-pyrrolidin-1-yl]-2,2,2-trifluoro-ethanone

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / Et₃N, DMAP, pyridine

2: AgClO₄, pyridine / tetrahydrofuran

With pyridine; dmap; silver perchlorate; triethylamine; In tetrahydrofuran;

DOI:10.1021/ja9600385

upstream raw materials:

1,4-dideoxy-1,4-imino-1-(S)-phenyl-D-ribitol

trifluoroacetic anhydride

Downstream raw materials:

1-{(2R,3R,4S,5S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-5-phenyl-pyrrolidin-1-yl}-2,2,2-trifluoro-ethanone

1-[(2R,3R,4S,5S)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-5-phenyl-pyrrolidin-1-yl]-2,2,2-trifluoro-ethanone

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