FMOC-(2S,3R)-3-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID

Base Information

• Chemical Name: FMOC-(2S,3R)-3-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID
• CAS No.: 281655-32-1
• Molecular Formula: C₂₆H₂₃NO₄
• Molecular Weight: 413.473
• Mol file: 281655-32-1.mol

Synonyms:(2S,3R)-3-phenyl-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester

Chemical Property of FMOC-(2S,3R)-3-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID

Chemical Property:

• Boiling Point: 626.3±55.0 °C(Predicted)
• PKA: 3.79±0.40(Predicted)
• Density: 1.299±0.06 g/cm3(Predicted)

Purity/Quality:

98%min ^*data from raw suppliers

Fmoc-(2S,3R)-3-phenylpyrrolidine-2-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of FMOC-(2S,3R)-3-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID

There total 1 articles about FMOC-(2S,3R)-3-PHENYLPYRROLIDINE-2-CARBOXYLIC ACID 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: 78.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (2S,3R)-3-phenyl-pyrrolidine-2-carboxylic acid (118758-48-8) → (2S,3R)-3-phenyl-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (281655-32-1,181824-45-3)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 18.0833h;

DOI:10.1016/j.bmc.2011.08.020

Reference yield:

(2S,3R)-3-phenyl-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (281655-32-1,181824-45-3) + (S)-2-[(S)-2-((S)-2-acetylamino-3-methyl-butyrylamino)-3-tert-butoxycarbonyl-propionylamino]-3-methyl-butyric acid (1344158-52-6) + C17H30N5O4Pol → (S)-3-((S)-2-acetamido-3-methylbutanamido)-4-(((S)-1-((2S,3R)-2-(((3S)-2-hydroxy-5-oxotetrahydrofuran-3-yl)carbamoyl)-3-phenylpyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-4-oxobutanoic acid (1344157-35-2)

Guidance literature:

(2S,3R)-3-phenyl-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester; C₁₇H₃₀N₅O₄Pol; With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 20h; solid phase reaction;

With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 1h; solid phase reaction;

(S)-2-[(S)-2-((S)-2-acetylamino-3-methyl-butyrylamino)-3-tert-butoxycarbonyl-propionylamino]-3-methyl-butyric acid; Further stages;

DOI:10.1016/j.bmc.2011.08.020

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + (2S,3R)-3-phenyl-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (281655-32-1,181824-45-3) + N-Fmoc L-Phe (35661-40-6) + Fmoc-(tBu)Asp-OH (71989-14-5) + Fmoc-Thr(tBu)-OH (71989-35-0,138797-71-4) → C52H73N9O17

Guidance literature:

Fmoc-Leu-OH; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; for 0.75h; Automated synthesizer;

With piperidine; In N,N-dimethyl-formamide; Automated synthesizer;

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; (2S,3R)-3-phenyl-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester; N-Fmoc L-Phe; Fmoc-(tBu)Asp-OH; Fmoc-Thr(tBu)-OH; Fmoc-Glu(Pg)-OH; Further stages;

DOI:10.1016/j.bmc.2020.115738

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

(2S,3R)-3-phenyl-pyrrolidine-2-carboxylic acid

Downstream raw materials:

(S)-3-((S)-2-acetamido-3-methylbutanamido)-4-(((S)-1-((2S,3R)-2-(((3S)-2-hydroxy-5-oxotetrahydrofuran-3-yl)carbamoyl)-3-phenylpyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-4-oxobutanoic acid

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