methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethoxyphosphoryl)acetate

• ChemBase ID: 63537
• Molecular Formular: C13H18NO7P
• Molecular Mass: 331.258281
• Monoisotopic Mass: 331.08208855
• SMILES: C(C(=O)OC)(NC(=O)OCc1ccccc1)P(=O)(OC)OC
• Canonical SMILES: COC(=O)C(P(=O)(OC)OC)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C13H18NO7P/c1-18-12(15)11(22(17,19-2)20-3)14-13(16)21-9-10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3,(H,14,16)
• InChIKey: GSYSFVSGPABNNL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethoxyphosphoryl)acetate
• IUPAC Traditional name: methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethoxyphosphoryl)acetate
• Synonyms: (±)-Methyl 2-benzyloxycarbonylamino-2-(dimethoxyphosphinyl) acetate; (±)-Trimethyl Z-α-phosphonoglycinate; (±)-Z-α-Phosphonoglycine trimethyl ester; Z-α-Phosphonoglycine trimethyl ester; Methyl 2-(benzyloxycarbonylamino)-2-dimethoxyphosphoryl-acetate; (±)-Z-α-Phosphonoglycine trimethyl ester; (+/-)-Cbz-alpha-phosphonoglycine trimethyl ester; Z-alpha-phosphonoglycine trimethyl ester; (±)-Benzyloxycarbonyl-alpha-phosphonoglycine trimethyl ester; (±)-Z-α-膦酰甘氨酸三甲酯; Z-α-膦酰甘氨酸三甲酯; (±)-三甲基 Z-α-膦酰甘氨酸酯; (±)-甲基 2-苄氧羰基氨基-2-(二甲氧基氧膦基)乙酸酯; (±)-Z-α-膦酰甘氨酸三甲酯; (+/-)-Cbz-α-膦酰基甘氨酸三甲酯

Database IDs

• CAS Number: 83026-99-7; 88568-95-0
• MDL Number: MFCD00043304
• Beilstein Number: 5764460
• PubChem SID: 24863436; 24890381; 162029276
• PubChem CID: 2734718

CALCULATED PROPERTIES

• Acid pKa: 12.7372055
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3748896
• LogD (pH = 7.4): 1.3748877
• Log P: 1.3748896
• Molar Refractivity: 75.9036 cm^3
• Polarizability: 30.744463 Å^3
• Polar Surface Area: 100.16 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 76-80°C; 77-80 °C(lit.); 78-80 °C

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: >95%; ≥97.0% (HPLC); 97%
• Grade: purum
• Linear Formula: (CH3O)2P(O)CH(NHCO2CH2C6H5)CO2CH3

DETAILS

Sigma Aldrich - C9794

Application
通过与醛发生 Wittig-Horner 反应合成 (Z)-脱氢氨基酸的原料；脱氢氨基酸可发生立体选择性还原反应生成氨基酸。

Sigma Aldrich - 376353

Application
Starting material for the synthesis of (Z)-dehydroamino acids by Wittig-Horner reaction with aldehydes; the dehydroamino acids can be stereoselectively reduced to amino acids.
Packaging
5 g in glass bottle

Sigma Aldrich - 97040

Application
Starting material for the synthesis of (Z)-dehydroamino acids by Wittig-Horner reaction with aldehydes; the dehydroamino acids can be stereoselectively reduced to amino acids.