(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)-N-(9'-phenylfluoren-9'-yl)pyrrolidine

Base Information

Chemical Name:(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)-N-(9'-phenylfluoren-9'-yl)pyrrolidine
CAS No.:160882-79-1
Molecular Formula:C₂₄H₂₃NO₃
Molecular Weight:373.452
Hs Code.:

Synonyms:(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)-N-(9'-phenylfluoren-9'-yl)pyrrolidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)-N-(9'-phenylfluoren-9'-yl)pyrrolidine

Chemical Property:

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Technology Process of (2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)-N-(9'-phenylfluoren-9'-yl)pyrrolidine

There total 7 articles about (2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)-N-(9'-phenylfluoren-9'-yl)pyrrolidine 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: 91.0%

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

: 160882-79-1
(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)-N-(9'-phenylfluoren-9'-yl)pyrrolidine

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; -78 degC, 40 min, room t., 2 h;
DOI:10.1016/S0040-4039(00)74441-8

Reference yield:

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

: 160882-79-1
(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)-N-(9'-phenylfluoren-9'-yl)pyrrolidine

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: 1.) LiEt₃BH, 2.) H₂O₂ (30percent), aq. LiOH / 1) THF, -78 deg C, rt, 2 h; 2) THF, 2 h, rt

With lithium hydroxide; chloro-trimethyl-silane; lead(II) nitrate; oxalyl dichloride; MoO₅*pyridine*HMPA; dihydrogen peroxide; sodium hexamethyldisilazane; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1021/jo9604245

Reference yield:

: 179990-59-1
(2S,4R)-4-hydroxy-N-(9'-phenylfluoren-9'-yl)pyrrolidine-2-carboxylic acid methyl ester

: 160882-79-1
(2R,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)-N-(9'-phenylfluoren-9'-yl)pyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -60 °C

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

3: 1.) LiEt₃BH, 2.) H₂O₂ (30percent), aq. LiOH / 1) THF, -78 deg C, rt, 2 h; 2) THF, 2 h, rt

With lithium hydroxide; oxalyl dichloride; MoO₅*pyridine*HMPA; dihydrogen peroxide; sodium hexamethyldisilazane; lithium triethylborohydride; dimethyl sulfoxide; In dichloromethane;
DOI:10.1021/jo9604245