(3R)-4-(benzyloxy)-3-{[(tert-butoxy)carbonyl]amino}butanoic acid

• ChemBase ID: 39383
• Molecular Formular: C16H23NO5
• Molecular Mass: 309.35752
• Monoisotopic Mass: 309.15762284
• SMILES: O(C[C@@H](CC(=O)O)NC(=O)OC(C)(C)C)Cc1ccccc1
• Canonical SMILES: OC(=O)C[C@@H](NC(=O)OC(C)(C)C)COCc1ccccc1
• InChI: InChI=1S/C16H23NO5/c1-16(2,3)22-15(20)17-13(9-14(18)19)11-21-10-12-7-5-4-6-8-12/h4-8,13H,9-11H2,1-3H3,(H,17,20)(H,18,19)/t13-/m1/s1
• InChIKey: BNSXKDBZQDOLAL-CYBMUJFWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-4-(benzyloxy)-3-{[(tert-butoxy)carbonyl]amino}butanoic acid
• IUPAC Traditional name: (3R)-4-(benzyloxy)-3-[(tert-butoxycarbonyl)amino]butanoic acid
• Synonyms: Boc-O-benzyl-L-beta-homoserine; Boc-O-benzyl-L-β-homoserine; Boc-β-Homoser(Bzl)-OH; Boc-O-苄基-L-β-高丝氨酸

Database IDs

• CAS Number: 218943-31-8
• MDL Number: MFCD01862866
• Beilstein Number: 8070512
• PubChem SID: 24845559; 161002690
• PubChem CID: 2761543

CALCULATED PROPERTIES

• Acid pKa: 4.4100194
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.1965536
• LogD (pH = 7.4): -0.5613589
• Log P: 2.3188992
• Molar Refractivity: 80.9021 cm^3
• Polarizability: 31.885212 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D +22.0±1.0°, 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

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C16H23NO5

DETAILS

Sigma Aldrich - 03697

Other Notes
Building block for the synthesis of L-β-homoserine-derived β2,3 -amino acids by β-alkylation and peptides containing these amino acids1