methyl (2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyacetate

• ChemBase ID: 145012
• Molecular Formular: C8H14O5
• Molecular Mass: 190.19376
• Monoisotopic Mass: 190.08412355
• SMILES: CC1(OC[C@H](O1)[C@H](C(=O)OC)O)C
• Canonical SMILES: COC(=O)[C@@H]([C@@H]1COC(O1)(C)C)O
• InChI: InChI=1S/C8H14O5/c1-8(2)12-4-5(13-8)6(9)7(10)11-3/h5-6,9H,4H2,1-3H3/t5-,6+/m0/s1
• InChIKey: JSFASCPVVJBLRD-NTSWFWBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyacetate
• IUPAC Traditional name: methyl (2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyacetate
• Synonyms: (αR,4S)-2,2-Dimethyl-α-hydroxy-1,3-dioxolane-4-acetic acid methyl ester; 3,4-O-Isopropylidene-L-threonic acid methyl ester; Methyl 3,4-O-isopropylidene-L-threonate; (αR,4S)-2,2-二甲基-α-羟基-1,3-二氧戊环-4-乙酸甲酯; 甲基3,4-O-异亚丙基-L-苏糖酸酯; 3,4-O-异亚丙基-L-苏糖酸甲酯

Database IDs

• CAS Number: 92973-40-5
• Beilstein Number: 7862
• PubChem SID: 162239222; 24864430
• PubChem CID: 10375250

CALCULATED PROPERTIES

• Acid pKa: 11.662942
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.30075607
• LogD (pH = 7.4): -0.30077943
• Log P: -0.30075577
• Molar Refractivity: 43.3221 cm^3
• Polarizability: 17.65504 Å^3
• Polar Surface Area: 64.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 125 °C/12 mmHg(lit.)
• Flash Point: 210.2 °F; 99 °C
• Density: 1.175 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.446(lit.)
• Optical Rotation: [α]20/D +18.5°, c = 2 in acetone

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C8H14O5

DETAILS

Sigma Aldrich - 392170

Packaging
5 g in glass bottle
Application
Used to prepare a dihydrofuran substrate in the total synthesis of (-)-echinosporin.1