(2S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoic acid

• ChemBase ID: 69916
• Molecular Formular: C11H13NO5
• Molecular Mass: 239.22462
• Monoisotopic Mass: 239.07937252
• SMILES: C(=O)([C@@H](NC(=O)OCc1ccccc1)CO)O
• Canonical SMILES: OC[C@@H](C(=O)O)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C11H13NO5/c13-6-9(10(14)15)12-11(16)17-7-8-4-2-1-3-5-8/h1-5,9,13H,6-7H2,(H,12,16)(H,14,15)/t9-/m0/s1
• InChIKey: GNIDSOFZAKMQAO-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoic acid
• IUPAC Traditional name: (2S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoic acid
• Synonyms: Carbobenzyloxy-L-serine; Z-L-Serine; N-Cbz-L-serine; N-Benzyloxycarbonyl-L-serine; Z-Ser-OH; (2S)-2-[(Benzyloxycarbonyl)amino]-3-hydroxypropanoic Acid; Benzyloxycarbonyl-L-serine; N-(Benzyloxycarbonyl)-L-serine; N-Carbobenzoxy-L-serine; N-Carbobenzyloxy-L-serine; N-[(Phenylmethoxy)carbonyl]serine; NSC 286604; N-Carboxy-L-serine N-Benzyl Ester; Z-Ser-OH; N-Cbz-L-Serine; N-苄氧羰基-L-丝氨酸; Z-L-丝氨酸; 苄氧羰基-L-丝氨酸

Database IDs

• CAS Number: 1145-80-8
• EC Number: 214-546-4
• MDL Number: MFCD00002662
• Beilstein Number: 2058314
• PubChem SID: 24888517; 162035641
• PubChem CID: 100310

CALCULATED PROPERTIES

• Acid pKa: 3.5838287
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.3739644
• LogD (pH = 7.4): -2.8116252
• Log P: 0.53698957
• Molar Refractivity: 57.721 cm^3
• Polarizability: 22.675972 Å^3
• Polar Surface Area: 95.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 116-119 °C; 116-119 °C(lit.); 117-120°C
• Optical Rotation: [α]20/D +5.8°, c = 2.7 in acetic acid; [α]20/D +6.0±0.5°, c = 7% in acetic acid; +6 (c=7 in acetic acid)

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false; 否
• Storage Temperature: -20°C

Product Information

• Purity: ≥99%; ≥99.0% (T); 95+%; 99%
• Grade: puriss.
• Linear Formula: HOCH2CH(NHCO2CH2C6H5)CO2H

DETAILS

Sigma Aldrich - C5252

Application
肽合成的结构单元；通过 β-内酯合成各种 α-氨基酸的原料1

Sigma Aldrich - 860700

Application
Building block in peptide synthesis; Starting material for the synthesis of various α-amino acids via the β-lactone1
Packaging
25 g in poly bottle

Sigma Aldrich - 97190

Application
Building block in peptide synthesis; Starting material for the synthesis of various α-amino acids via the β-lactone1

Toronto Research Chemicals - C182415

Building block in peptide synthesis.

REFERENCES

• Pansare, S. V.; Org. Synth. 70, 10(1992)
• Mitsunobu conversion to the ?-lactone and subsequent reaction with pyrazole is an example of a versatile route to N-protected ɑ-amino acids: Org. Synth. Coll., 9, 58 (1998) and references therein:
  
• For a different synthesis of racemic pyrazoloaniline, see 2-Acetamidoacrylic acid, L01649.