(3R,5S)-1-(tert-butoxycarbonyl)-5-hydroxymethyl-3-phenylseleno-2-pyrrolidinone

Base Information

• Chemical Name: (3R,5S)-1-(tert-butoxycarbonyl)-5-hydroxymethyl-3-phenylseleno-2-pyrrolidinone
• CAS No.: 132430-60-5
• Molecular Formula: C₁₆H₂₁NO₄Se
• Molecular Weight: 370.307

Synonyms:(3R,5S)-1-(tert-butoxycarbonyl)-5-hydroxymethyl-3-phenylseleno-2-pyrrolidinone

Chemical Property of (3R,5S)-1-(tert-butoxycarbonyl)-5-hydroxymethyl-3-phenylseleno-2-pyrrolidinone

Chemical Property:

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Technology Process of (3R,5S)-1-(tert-butoxycarbonyl)-5-hydroxymethyl-3-phenylseleno-2-pyrrolidinone

There total 2 articles about (3R,5S)-1-(tert-butoxycarbonyl)-5-hydroxymethyl-3-phenylseleno-2-pyrrolidinone 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: 81.0%

(S)-2-Oxo-3-phenylselanyl-5-trityloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (124665-88-9,124665-89-0,126179-15-5,126179-25-7) → (3RS,5S)-1-(tert-butoxycarbonyl)-5-hydroxymethyl-3-phenylseleno-2-pyrrolidinone (132430-60-5,132430-69-4)

Guidance literature:

With hydrogenchloride; In methanol; at 40 ℃; for 2h;

DOI:10.1248/cpb.38.2712

Reference yield: 71.0%

(3R,5S)-1-(tert-butoxycarbonyl)-3-phenylseleno-5-trityloxymethyl-2-pyrrolidinone (126179-15-5) → (3R,5S)-1-(tert-butoxycarbonyl)-5-hydroxymethyl-3-phenylseleno-2-pyrrolidinone (132430-60-5)

Guidance literature:

With hydrogenchloride; In methanol; at 30 - 35 ℃; for 1h;

DOI:10.1248/cpb.40.1925

Reference yield: 45.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (3R,5S)-1-(tert-butoxycarbonyl)-5-hydroxymethyl-3-phenylseleno-2-pyrrolidinone (132430-60-5) → (3R,5S)-1-(tert-butoxycarbonyl)-5-methoxymethyl-3-phenylseleno-2-pyrrolidinone (145221-01-8)

Guidance literature:

With tetrafluoroboric acid; In dichloromethane; at 0 ℃; for 0.05h;

DOI:10.1248/cpb.40.1925

upstream raw materials:

(S)-2-Oxo-3-phenylselanyl-5-trityloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

(3R,5S)-1-(tert-butoxycarbonyl)-3-phenylseleno-5-trityloxymethyl-2-pyrrolidinone

Downstream raw materials:

(2RS,4S)-4-<(tert-butoxycarbonyl)amino>-2-phenylseleno-5-pentanolide

swainsonine

(2R,3S,4R)-N-benzyl-3,4-bis(benzyloxy)-2-hydroxymethylpyrrolidine

(2S,3S,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidine-2-carbaldehyde

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