3-tert-butyl 4-methyl (4S)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate

• ChemBase ID: 75063
• Molecular Formular: C12H21NO5
• Molecular Mass: 259.29884
• Monoisotopic Mass: 259.14197278
• SMILES: O=C([C@H]1N(C(=O)OC(C)(C)C)C(C)(C)OC1)OC
• Canonical SMILES: COC(=O)[C@@H]1COC(N1C(=O)OC(C)(C)C)(C)C
• InChI: InChI=1S/C12H21NO5/c1-11(2,3)18-10(15)13-8(9(14)16-6)7-17-12(13,4)5/h8H,7H2,1-6H3/t8-/m0/s1
• InChIKey: ZNBUXTFASGDVCL-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-tert-butyl 4-methyl (4S)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate
• IUPAC Traditional name: 3-tert-butyl 4-methyl (4S)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate
• Synonyms: Methyl (S)-(-)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate; Methyl (S)-(-)-3-Boc-2,2-dimethyl-4-oxazolidinecarboxylate; (S)-3-(1,1-Dimethylethyl)-4-methyl-2,2-dimethyl-3,4-oxazolidine carboxylate; methyl (s)-(-)-3-boc-2,2-dimethyl-4-oxazolidinecarboxylate; (S)-(-)-3-tert-Butoxycarbonyl-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine; 3-tert-Butyl 4-methyl (4R)-(+)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate; (4R)-(+)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-(methoxycarbonyl)-1,3-oxazolidine; Methyl (4R)-(+)-2,2-dimethyl-1,3-oxazolidine-4-carboxylate, N-BOC protected; (S)-(-)-3-(叔丁氧羰基)-2,2-二甲基-4-噁唑啉羧酸甲酯; (S)-(-)-3-Boc-2,2-二甲基-4-噁唑啉羧酸甲酯

Database IDs

• CAS Number: 95715-86-9; 108149-60-6
• MDL Number: MFCD00192279; MFCD00674041
• PubChem SID: 162039981; 24865525
• PubChem CID: 688221

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.2953444
• LogD (pH = 7.4): 1.2953444
• Log P: 1.2953444
• Molar Refractivity: 64.0356 cm^3
• Polarizability: 25.56365 Å^3
• Polar Surface Area: 65.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 101-102 °C/2 mmHg(lit.); 89°C
• Flash Point: 199.4 °F; 93 °C; 93°C
• Density: 1.082; 1.082 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.443(lit.)
• Optical Rotation: [α]20/D -55°, c = 1.3 in chloroform

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 95+%; 98%
• Optical Purity: ee: 99% (HPLC)
• Empirical Formula (Hill Notation): C12H21NO5

DETAILS

Sigma Aldrich - 410438

Packaging
1, 5 g in glass bottle
Application
Precursor to a configurationally stable serinal derivative (Garner′s aldehyde) that has been used to make azasugars, sphingolipids, and the amino sugar found in calicheamicin, a potent antitumor agent.1,2,3,4,5