203866-20-0

Basic information

• Product Name: FMOC-TRANS-4-FLUORO-PRO-OH
• Synonyms: N-FMOC-TRANS-4-FLUORO-L-PROLINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-(2S,4R)-4-FLUORO-PYRROLIDINE-2-CARBOXYLIC ACID;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-TRANS-4-FLUORO-L-PROLINE;FMOC-TRANS-4-FLUORO-L-PROLINE;FMOC-TRANS-4-FLUORO-PROLINE;FMOC-TRANS-4-FLUORO-PRO-OH;FMOC-PRO(4-F)-OH;FMOC-(2S,4R)-PRO(4-F)-OH
• CAS NO: 203866-20-0
• Molecular Formula: C₂₀H₁₈FNO₄
• Molecular Weight: 355.36
• Mol File: 203866-20-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 556.024 °C at 760 mmHg
• Flash Point: 290.073 °C
• Appearance: /
• Density: 1.403 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.646
• Storage Temp.: Store at?0-5°C
• PKA: 3.48±0.40(Predicted)
• CAS DataBase Reference: FMOC-TRANS-4-FLUORO-PRO-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-TRANS-4-FLUORO-PRO-OH(203866-20-0)
• EPA Substance Registry System: FMOC-TRANS-4-FLUORO-PRO-OH(203866-20-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 203866-20-0(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white solid

InChI:InChI=1/C20H18FNO4/c21-12-9-18(19(23)24)22(10-12)20(25)26-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,12,17-18H,9-11H2,(H,23,24)/t12-,18+/m1/s1

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 2438-57-5 (2S,4R)-4-fluoropyrrolidine-2-carboxylic acid 
• 203866-18-6 methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate 
• 203866-14-2 (2S,4R)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid 
• 129430-93-9 (2S,4S)-methyl 4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 129430-93-9 methyl (2S,4R)-4-hydroxy-1-tritylpyrrolidine-2-carboxylate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 51-35-4 4R-4-hydroxyproline 
• 99465-82-4 (2S,4R)-methyl 4-hydroxy-1-pivaloylpyrrolidine-2-carboxylate 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 149671-25-0 1-(2,2-dimethyl-propionyl)-4-hydroxy-pyrrolidine-2-carboxylic acid 
• 497073-98-0 4-fluoro-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-(2-oxo-2-phenyl-ethyl) ester 

Downstream Products

• 1440521-95-8 C₃₉H₆₅FN₁₂O₈ 

Relevant articles and documents

Evidence for a stereoelectronic effect in human oxygen sensing

How PHDs achieve specificity: trans-4-prolyl hydroxylation of the transcription factor HIF occurs with stereochemical retention. Substrate-analogue studies show how the von Hippel Lindau tumor suppressor protein (pVHL) and the oxygen-sensing hydroxylases (PHDs) achieve specificity for hydroxy prolyl/prolyl residues for the C4-exo/endo prolyl conformations, respectively.

Practical synthesis of Boc and Fmoc protected 4-fluoro and 4-difluoroprolines from trans-4-hydroxyproline

Boc-cis-4-fluoro-L-proline and 4-difluoro-L-proline, usable in classical peptide synthesis, were obtained in respectively 71% (3 steps) and 65% (4 steps) overall yields from the readily available trans-4-hydroxy-L-proline methyl ester. The corresponding fluorinated trans-isomer was isolated in 24% yield (5 steps). Transformation of Boc-protected compounds to their Fmoc-equivalents was performed in high yields.