(2S)-3-{[(benzyloxy)(hydroxy)phosphoryl]oxy}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid

• ChemBase ID: 157820
• Molecular Formular: C25H24NO8P
• Molecular Mass: 497.433721
• Monoisotopic Mass: 497.12395336
• SMILES: c1ccc(cc1)COP(=O)(O)OC[C@@H](C(=O)O)NC(=O)OCC1c2ccccc2c2c1cccc2
• Canonical SMILES: O=C(N[C@H](C(=O)O)COP(=O)(OCc1ccccc1)O)OCC1c2ccccc2c2c1cccc2
• InChI: InChI=1S/C25H24NO8P/c27-24(28)23(16-34-35(30,31)33-14-17-8-2-1-3-9-17)26-25(29)32-15-22-20-12-6-4-10-18(20)19-11-5-7-13-21(19)22/h1-13,22-23H,14-16H2,(H,26,29)(H,27,28)(H,30,31)/t23-/m0/s1
• InChIKey: ZBPUWGDUVAAWJY-QHCPKHFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-{[(benzyloxy)(hydroxy)phosphoryl]oxy}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid
• IUPAC Traditional name: (2S)-3-{[benzyloxy(hydroxy)phosphoryl]oxy}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid
• Synonyms: Fmoc-O-(benzylphospho)-L-serine; Fmoc-Ser(PO3BzlH)-OH; N-芴甲氧羰基-O-(苄基磷酰基)-L-丝氨酸

Database IDs

• CAS Number: 158171-14-3
• MDL Number: MFCD00797869
• Beilstein Number: 7060483
• PubChem SID: 24846403; 162251957
• PubChem CID: 11005563

CALCULATED PROPERTIES

• Acid pKa: 1.8673959
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.25387633
• LogD (pH = 7.4): -1.735691
• Log P: 3.977275
• Molar Refractivity: 126.0886 cm^3
• Polarizability: 50.573917 Å^3
• Polar Surface Area: 131.39 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C25H24NO8P

DETAILS

Sigma Aldrich - 09769

Other Notes
Synthesis of phosphopeptides1,2,3