(2S)-4-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}-4-oxobutanoic acid

• ChemBase ID: 38418
• Molecular Formular: C16H21NO6
• Molecular Mass: 323.34104
• Monoisotopic Mass: 323.1368874
• SMILES: C(=O)(C[C@@H](C(=O)O)NC(=O)OC(C)(C)C)OCc1ccccc1
• Canonical SMILES: O=C(C[C@@H](C(=O)O)NC(=O)OC(C)(C)C)OCc1ccccc1
• InChI: InChI=1S/C16H21NO6/c1-16(2,3)23-15(21)17-12(14(19)20)9-13(18)22-10-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,21)(H,19,20)/t12-/m0/s1
• InChIKey: SOHLZANWVLCPHK-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}-4-oxobutanoic acid
• IUPAC Traditional name: (2S)-4-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoic acid
• Synonyms: N-(tert-Butoxycarbonyl)-L-aspartic acid 4-benzyl ester; Boc-L-aspartic acid 4-benzyl ester; Boc-Asp(OBzl)-OH; Boc-Asp-OBzl; N-α-t-BOC-L-ASPARTIC ACID BENZYL ESTER; N-Alpha-t-Boc-L-aspartic acid beta-benzyl ester; N-(叔丁氧羰基)-L-天冬氨酸-4-苄酯; Boc-L-天冬氨酸-4-苄酯

Database IDs

• CAS Number: 7536-58-5
• EC Number: 231-406-8
• MDL Number: MFCD00065564
• Beilstein Number: 2064127
• PubChem SID: 24849383; 24867616; 161001725
• PubChem CID: 1581888

CALCULATED PROPERTIES

• Acid pKa: 3.757916
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.3990914
• LogD (pH = 7.4): -1.1392635
• Log P: 2.1419413
• Molar Refractivity: 80.7874 cm^3
• Polarizability: 32.006542 Å^3
• Polar Surface Area: 101.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 98-102 °C(lit.)
• Optical Rotation: [α]20/D -19.5°, c = 2 in DMF; [α]20/D -20.0±1°, c = 2% in DMF

Safety Information

• Storage Condition: 0°C
• 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: ≥99.0% (sum of enantiomers, HPLC); 98%
• Linear Formula: C6H5CH2OCOCH2CH(COOH)NHCOOC(CH3)3

DETAILS

MP Biomedicals - 02101067

Crystalline

Sigma Aldrich - 440655

Application
Starting material for the enantiospecific synthesis of (R)-(+)-Boc-iturinic acid (n-C14),1 the L-aspartic series of thrombin inhibitors,2 and diketopiperazine tetrapeptides.3 Used in the preparation of a novel tricyclic dipeptide mimetic based on a [6H]-azepino indoline nucleus.4
Packaging
25 g in glass bottle

Sigma Aldrich - 15386

Packaging
5, 25 g in glass bottle