methyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate

• ChemBase ID: 152210
• Molecular Formular: C8H14O4
• Molecular Mass: 174.19436
• Monoisotopic Mass: 174.08920893
• SMILES: C[C@H]1[C@@H](OC(O1)(C)C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1OC(O[C@H]1C)(C)C
• InChI: InChI=1S/C8H14O4/c1-5-6(7(9)10-4)12-8(2,3)11-5/h5-6H,1-4H3/t5-,6+/m0/s1
• InChIKey: AELKYRWKHKGMAD-NTSWFWBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate
• IUPAC Traditional name: methyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate
• Synonyms: 4-Deoxy-2,3-O-isopropylidene-L-threonic acid methyl ester; Methyl (2R,3S)-2,3-O-isopropylidene-2,3-dihydroxybutyrate; Methyl 4-deoxy-2,3-O-isopropylidene-L-threonate; Methyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate; (2R,3S)-2,3-O-异亚丙基-2,3-二羟基丁酸甲酯; 4-脱氧-2,3-O-异亚丙基-L-苏糖酸甲基酯; 4-脱氧-2,3-O-异亚丙基-L-苏糖酸甲酯; (4R,5S)-2,2,5-三甲基-1,3-二氧戊环-4-羧酸甲酯

Database IDs

• CAS Number: 78086-72-3
• MDL Number: MFCD00077802
• Beilstein Number: 4667377
• PubChem SID: 162246355; 24881500
• PubChem CID: 853434

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.7461542
• LogD (pH = 7.4): 0.7461542
• Log P: 0.7461542
• Molar Refractivity: 41.7784 cm^3
• Polarizability: 16.966852 Å^3
• Polar Surface Area: 44.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 122 °F; 50 °C
• Density: 1.06 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.422
• Optical Rotation: [α]20/D +19±1°, c = 4% in chloroform

Safety Information

• UN Number: 1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 10
• GHS Pictograms: GHS02
• GHS Signal Word: Warning
• GHS Hazard statements: H226
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3

Product Information

• Purity: ≥90% (sum of enantiomers, GC)
• Grade: technical
• Empirical Formula (Hill Notation): C8H14O4

DETAILS

Sigma Aldrich - 59436

Other Notes
Chiral building block: stereoselective α-alkylation.1 Preparation of the corresponding aldehyde.2,3
Packaging
5 mL in glass bottle