tert-butyl (4S)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

• ChemBase ID: 150548
• Molecular Formular: C11H19NO4
• Molecular Mass: 229.27286
• Monoisotopic Mass: 229.13140809
• SMILES: CC1(N([C@@H](CO1)C=O)C(=O)OC(C)(C)C)C
• Canonical SMILES: O=C[C@@H]1COC(N1C(=O)OC(C)(C)C)(C)C
• InChI: InChI=1S/C11H19NO4/c1-10(2,3)16-9(14)12-8(6-13)7-15-11(12,4)5/h6,8H,7H2,1-5H3/t8-/m1/s1
• InChIKey: PNJXYVJNOCLJLJ-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl (4S)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• IUPAC Traditional name: tert-butyl (4S)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• Synonyms: (-)-N-Boc-N,O-isopropylidene-L-serinal; tert-Butyl (S)-(-)-4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate; Garner’s aldehyde; (S)-(-)-3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde; (4R)-4-Formyl-2,2-dimethyl-3-oxazolidinecarboxylic Acid 1,1-Dimethylethyl Ester; (4R)-4-Formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylic Acid tert-Butyl Ester; (R)-Garner Aldehyde; tert-Butyl (R)-4-Formyl-2,2-dimethyloxazolidine-3-carboxylate; (+)-N-Boc-N,O-isopropylidene-D-serinal; (4R)-3-tert-Butoxycarbonyl-2,2-dimethyl-4-formyloxazolidine; (S)-(-)-3-tert-Butoxycarbonyl-2,2-dimethyloxazolidine-4-carboxaldehyde; Garner's Aldehyde; tert-Butyl (S)-(-)-4-formyl-2,2-Dimethyl-3-oxazolidinecarboxylate; (S)-4-Formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester; (s)-3-boc-4-formyl-2,2-dimethyl-1,3-oxazolidine; tert-butyl (s)-(-)-4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate; (-)-N-Boc-N,O-异亚丙基-L-丝氨醛; (S)-(-)-4-甲酰基-2,2-二甲基-3-噁唑啉羧酸叔丁酯; Garner 醛; (S)-(-)-3-Boc-2,2-二甲基噁唑烷-4-甲醛; (S)-(-)-3-Boc-2,2-二甲基唑烷-4-甲醛

Database IDs

• CAS Number: 95715-87-0; 102308-32-7
• MDL Number: MFCD00209557
• Beilstein Number: 3591324
• Merck Index: 144371
• PubChem SID: 24867096; 162244709
• PubChem CID: 179824

CALCULATED PROPERTIES

• Acid pKa: 14.5326
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.99083406
• LogD (pH = 7.4): 0.990834
• Log P: 0.99083406
• Molar Refractivity: 58.3411 cm^3
• Polarizability: 22.996452 Å^3
• Polar Surface Area: 55.84 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Colourless Oil
• Boiling Point: 83-88 °C/1 mmHg(lit.)
• Flash Point: 108 °C; 226.4 °F
• Density: 1.06; 1.06 g/mL at 25 °C(lit.)
• Refractive Index: 1.4450; n20/D 1.445(lit.)
• Optical Rotation: [α]20/D -90°, c = 1 in chloroform; -90 (c=1 in chloroform)

Safety Information

• Storage Warning: Air Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 95%; 95+%; 98%
• Empirical Formula (Hill Notation): C11H19NO4

DETAILS

Sigma Aldrich - 432741

Application
Widely utilized in the asymmetric synthesis of natural products.1,2,3
Packaging
1 g in glass bottle

Toronto Research Chemicals - B690120

Intermediate in the preparation of various enzymatic inhibitors.

REFERENCES

• Bogen, S., et al.: Bioorg. Med. Chem. Lett., 18, 4219 (2008)
• Pinto, A., et al.: J. Med. Chem., 51, 2311 (2008)
• Bogen, S., et al.: Bioorg. Med. Chem., 18, 1854 (2008)