(2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester
CAS No.:179990-60-4
Molecular Formula:C₂₅H₂₃NO₄
Molecular Weight:401.462
Hs Code.:

Synonyms:(2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

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Chemical Property of (2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

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Technology Process of (2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

There total 7 articles about (2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester 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: 92.0%

: 160882-77-9
(2S,3S)-3-hydroxy-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

: 179990-60-4
(2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -78 ℃; for 4h;
DOI:10.1021/jo9604245

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 179990-60-4
(2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) chlorotrimethylsilane, Et₃N, 2.) Et₃N, Pb(NO₃)2 / 1) CH₂Cl₂, reflux, 1 h; 2) CH₂Cl₂, MeOH, rt, 96 h

2: 100 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -60 °C

3: 1.) NaHMDS, 2.) MoOPH / 1) THF, -78 deg C, 2 h; 2) THF, -78 - -15 deg C, 2.5 h

4: 92 percent / NaBH₄ / methanol; tetrahydrofuran / 4 h / -78 °C

With sodium tetrahydroborate; chloro-trimethyl-silane; lead(II) nitrate; oxalyl dichloride; MoO₅*pyridine*HMPA; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo9604245

Reference yield:

: 160882-76-8
(2S)-4-oxo-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

: 179990-60-4
(2S,3S,4R)-3,4-dihydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) NaHMDS, 2.) MoOPH / 1) THF, -78 deg C, 2 h; 2) THF, -78 - -15 deg C, 2.5 h

2: 92 percent / NaBH₄ / methanol; tetrahydrofuran / 4 h / -78 °C

With sodium tetrahydroborate; MoO₅*pyridine*HMPA; sodium hexamethyldisilazane; In tetrahydrofuran; methanol;
DOI:10.1021/jo9604245