205526-24-5

Basic information

• Product Name: FMOC-L-3,5-DIFLUOROPHE
• Synonyms: FMOC-L-3,5-DIFLUOROPHE;FMOC-L-3,5-DIFLUOROPHENYLALANINE;FMOC-PHE(3,5-DIF)-OH;FMOC-PHE(3,5-F 2)-OH;FMOC-PHE(M-F2)-OH;FMOC-3,5-DIFLUORO-L-PHENYLALANINE;3,5-DIFLUORO-L-PHENYLALANINE, FMOC PROTECTED;(S)-3-(3,5-DIFLUORO-PHENYL)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-PROPIONIC ACID
• CAS NO: 205526-24-5
• Molecular Formula: C₂₄H₁₉F₂NO₄
• Molecular Weight: 423.41
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;Peptide
• Mol File: 205526-24-5.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 610.7 °C at 760 mmHg
• Flash Point: 323.1 °C
• Appearance: /
• Density: 1.357 g/cm³
• Vapor Pressure: 9.12E-16mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: Store at 0°C
• PKA: 3.62±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: FMOC-L-3,5-DIFLUOROPHE(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-3,5-DIFLUOROPHE(205526-24-5)
• EPA Substance Registry System: FMOC-L-3,5-DIFLUOROPHE(205526-24-5)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• Hazardous Substances Data: 205526-24-5(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white crystalline powder

Uses

3,5-Difluoro-N-Fmoc-L-phenylalanine is used for producing high quality peptides.

InChI:InChI=1/C24H19F2NO4/c25-15-9-14(10-16(26)12-15)11-22(23(28)29)27-24(30)31-13-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-10,12,21-22H,11,13H2,(H,27,30)(H,28,29)/t22-/m1/s1

Synthetic route

E-hept-2-enoic acid (10352-88-2) + Fmoc-3,5-difluoro-L-phenylalanine (205526-24-5) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) + C40H33ClNO4Pol + Fmoc-Pro-OH (71989-31-6) + Fmoc-Ser(Trt)-OH (111061-56-4) → C38H52F2N6O9

Conditions

Yield

Stage #1: C40H33ClNO4Pol With piperidine In N,N-dimethyl-formamide for 0.25h; 2-chlorotrityl resin; Stage #2: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 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 In 1-methyl-pyrrolidin-2-one Stage #3: E-hept-2-enoic acid; Fmoc-3,5-difluoro-L-phenylalanine; Fmoc-Pro-OH; Fmoc-Ser(Trt)-OH Further stages;

93%

E-hept-2-enoic acid (10352-88-2) + Fmoc-3,5-difluoro-L-phenylalanine (205526-24-5) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) + C40H33ClNO4Pol + Fmoc-Pro-OH (71989-31-6) + (S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (101555-63-9, 105751-19-7, 86069-86-5) + Fmoc-Ser(Trt)-OH (111061-56-4) → C39H54F2N6O9

Conditions

Yield

Stage #1: C40H33ClNO4Pol With piperidine In N,N-dimethyl-formamide for 0.25h; 2-chlorotrityl resin; Stage #2: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 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 In 1-methyl-pyrrolidin-2-one Stage #3: E-hept-2-enoic acid; Fmoc-3,5-difluoro-L-phenylalanine; Fmoc-Pro-OH; (S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid; Fmoc-Ser(Trt)-OH Further stages;

85%

E-hept-2-enoic acid (10352-88-2) + Fmoc-3,5-difluoro-L-phenylalanine (205526-24-5) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) + C40H33ClNO4Pol + Fmoc-Pro-OH (71989-31-6) + N-(9-fluorenylmethoxycarbonyl)-N-methyl-L-alanine (84000-07-7) + Fmoc-Ser(Trt)-OH (111061-56-4) → C37H52F2N6O9

Conditions

Yield

Stage #1: C40H33ClNO4Pol With piperidine In N,N-dimethyl-formamide for 0.25h; 2-chlorotrityl resin; Stage #2: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 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 In 1-methyl-pyrrolidin-2-one Stage #3: E-hept-2-enoic acid; Fmoc-3,5-difluoro-L-phenylalanine; Fmoc-Pro-OH; N-(9-fluorenylmethoxycarbonyl)-N-methyl-L-alanine; Fmoc-Ser(Trt)-OH Further stages;

81%

E-hept-2-enoic acid (10352-88-2) + Fmoc-3,5-difluoro-L-phenylalanine (205526-24-5) + C40H33ClNO4Pol + Fmoc-Pro-OH (71989-31-6) + (S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (101555-63-9, 105751-19-7, 86069-86-5) + Fmoc-Ser(Trt)-OH (111061-56-4) + (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)butanoic acid (135112-27-5) → C40H56F2N6O9

Conditions

Yield

Stage #1: C40H33ClNO4Pol With piperidine In N,N-dimethyl-formamide for 0.25h; 2-chlorotrityl resin; Stage #2: (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)butanoic acid 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 In 1-methyl-pyrrolidin-2-one Stage #3: E-hept-2-enoic acid; Fmoc-3,5-difluoro-L-phenylalanine; Fmoc-Pro-OH; (S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid; Fmoc-Ser(Trt)-OH Further stages;

77%

(2S,4R)-trans-N-(9-fluorenylmethoxycarbonyl)-4-methylproline + E-hept-2-enoic acid (10352-88-2) + Fmoc-3,5-difluoro-L-phenylalanine (205526-24-5) + C20H17N3O4 + (S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid (101555-63-9, 105751-19-7, 86069-86-5) + Fmoc-L-propargyl-Gly-OH (198561-07-8) + Fmoc-serine(pg) → C41H52F2N8O9

Conditions	Yield
Stage #1: (2S,4R)-trans-N-(9-fluorenylmethoxycarbonyl)-4-methylproline Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #3: E-hept-2-enoic acid; Fmoc-3,5-difluoro-L-phenylalanine; C20H17N3O4; (S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidine-2-carboxylic acid; Fmoc-L-propargyl-Gly-OH; Fmoc-serine(pg) Further stages;	76%

E-hept-2-enoic acid (10352-88-2) + Fmoc-3,5-difluoro-L-phenylalanine (205526-24-5) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) + C40H33ClNO4Pol + Fmoc-Pro-OH (71989-31-6) + (S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (136030-33-6) + Fmoc-Ser(Trt)-OH (111061-56-4) → C43H54F2N6O9

Conditions

Yield

Stage #1: C40H33ClNO4Pol With piperidine In N,N-dimethyl-formamide for 0.25h; 2-chlorotrityl resin; Stage #2: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 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 In 1-methyl-pyrrolidin-2-one Stage #3: E-hept-2-enoic acid; Fmoc-3,5-difluoro-L-phenylalanine; Fmoc-Pro-OH; (S)-2-(((9H-fluoren-9-yl)methoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; Fmoc-Ser(Trt)-OH Further stages;

72%