methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropanoate

• ChemBase ID: 69480
• Molecular Formular: C9H17NO5
• Molecular Mass: 219.23498
• Monoisotopic Mass: 219.11067265
• SMILES: C(=O)([C@H](NC(=O)OC(C)(C)C)CO)OC
• Canonical SMILES: OC[C@H](C(=O)OC)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C9H17NO5/c1-9(2,3)15-8(13)10-6(5-11)7(12)14-4/h6,11H,5H2,1-4H3,(H,10,13)/t6-/m1/s1
• InChIKey: SANNKFASHWONFD-ZCFIWIBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropanoate
• IUPAC Traditional name: methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropanoate
• Synonyms: tert-Butyl [(R)-1-(Methoxycarbonyl)-2-hydroxyethyl]carbamate; (R)-Methyl 2-(tert-Butoxycarbonylamino)-3-hydroxypropanoate; N-[(1,1-Dimethylethoxy)carbonyl]-D-serine Methyl Ester; N-tert-Butoxycarbonyl-D-Serine Methyl Ester; N-(tert-Butoxycarbonyl)-D-serine methyl ester; Boc-D-Serine methyl ester; N-(叔丁氧基羰基)-D-丝氨酸甲酯

Database IDs

• CAS Number: 95715-85-8
• MDL Number: MFCD00270516
• PubChem SID: 162035206; 24868220
• PubChem CID: 377723

CALCULATED PROPERTIES

• Acid pKa: 13.126097
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.012370152
• LogD (pH = 7.4): 0.012369436
• Log P: 0.012370162
• Molar Refractivity: 51.6831 cm^3
• Polarizability: 20.737991 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Clear Colorless Oil
• Boiling Point: 215 °C(lit.)
• Flash Point: 113 °C; 235 °F
• Density: 1.08 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.453(lit.)
• Optical Rotation: [α]25/D +18.8°, c = 5 in methanol

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false

Product Information

• Purity: 95+%; 97%
• Linear Formula: HOCH2CH[NHCO2C(CH3)3]CO2CH3

DETAILS

Sigma Aldrich - 446068

Packaging
1, 10 g in glass bottle

Toronto Research Chemicals - B690475

Protected D-Serine.

REFERENCES

• Micale, N., et al.: J. Med. Chem., 49, 3064 (2006)
• Gauthier, J., et al.: Bioorg. Med. Chem. Lett., 18, 923 (2006)