(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[(9H-xanthen-9-yl)carbamoyl]propanoic acid

• ChemBase ID: 38411
• Molecular Formular: C22H24N2O6
• Molecular Mass: 412.43576
• Monoisotopic Mass: 412.1634365
• SMILES: N(C(=O)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C)C1c2c(Oc3c1cccc3)cccc2
• Canonical SMILES: O=C(NC1c2ccccc2Oc2c1cccc2)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C22H24N2O6/c1-22(2,3)30-21(28)23-15(20(26)27)12-18(25)24-19-13-8-4-6-10-16(13)29-17-11-7-5-9-14(17)19/h4-11,15,19H,12H2,1-3H3,(H,23,28)(H,24,25)(H,26,27)/t15-/m0/s1
• InChIKey: YMGDQLXBNMRJMR-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[(9H-xanthen-9-yl)carbamoyl]propanoic acid
• IUPAC Traditional name: (2S)-2-[(tert-butoxycarbonyl)amino]-3-[(9H-xanthen-9-yl)carbamoyl]propanoic acid
• Synonyms: Boc-Asn(Xan)-OH; Nα-t-Boc-Nγ-Xanthyl-L-asparagine; Nα-Boc-Nγ-(9-xanthenyl)-L-asparagine; Nα-Boc-Nβ-xanthenyl-L-asparagine; N-Boc-N'-xanthyl-L-asparagine; N-Alpha-t-Boc-N-beta-xanthyl-L-asparagine; Nα-Boc-Nγ-xanthyl-L-asparagine; Boc-Asn(Xan)-OH; Nα-t-Boc-Nγ-占吨基-L-天门冬酰胺; Nα-叔丁氧羰基-Nγ-(氧蒽基)-L-天门冬酰胺; Nα-Boc-Nβ-占吨基-L-天门冬酰胺; Nα-Boc-Nγ-(9-氧杂蒽基)-L-天冬酰胺; Nα-Boc-Nγ-呫吨基-L-天冬酰胺

Database IDs

• CAS Number: 65420-40-8
• MDL Number: MFCD00066157
• Beilstein Number: 5172403
• PubChem SID: 24849424; 161001718
• PubChem CID: 7017974

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.7194188
• LogD (pH = 7.4): -0.655311
• Log P: 2.7240622
• Molar Refractivity: 107.2028 cm^3
• Polarizability: 42.00415 Å^3
• Polar Surface Area: 113.96 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true
• Acid pKa: 3.486507

PROPERTIES

Physical Property

• Melting Point: ~176 °C (dec.); 177.5-181.5 °C(lit.)
• Optical Rotation: [α]20/D +3°, c = 1 in acetone; [α]20/D +9.2±0.5°, c = 1% in methanol

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, TLC); 95+%; 96%
• Empirical Formula (Hill Notation): C22H24N2O6

DETAILS

Sigma Aldrich - 533149

Packaging
1, 5 g in glass bottle