(3S,4R,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyoxolan-2-one

• ChemBase ID: 152075
• Molecular Formular: C9H14O6
• Molecular Mass: 218.20386
• Monoisotopic Mass: 218.07903817
• SMILES: CC1(OC[C@H](O1)[C@@H]1[C@@H]([C@@H](C(=O)O1)O)O)C
• Canonical SMILES: O=C1O[C@@H]([C@@H]([C@@H]1O)O)[C@@H]1COC(O1)(C)C
• InChI: InChI=1S/C9H14O6/c1-9(2)13-3-4(15-9)7-5(10)6(11)8(12)14-7/h4-7,10-11H,3H2,1-2H3/t4-,5+,6-,7+/m0/s1
• InChIKey: JNTPPVKRHGNFKM-BNHYGAARSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyoxolan-2-one
• IUPAC Traditional name: (3S,4R,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxyoxolan-2-one
• Synonyms: 5,6-O-Isopropylidene-L-gulonic acid γ-lactone; 5,6-O-异亚丙基-L-古洛糖酸 γ-内酯

Database IDs

• CAS Number: 94697-68-4
• MDL Number: MFCD00077804
• Beilstein Number: 5267697
• PubChem SID: 162246220; 24881529
• PubChem CID: 10867731

CALCULATED PROPERTIES

• Acid pKa: 11.632735
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.042849
• LogD (pH = 7.4): -1.042874
• Log P: -1.0428486
• Molar Refractivity: 46.9858 cm^3
• Polarizability: 19.47009 Å^3
• Polar Surface Area: 85.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 166-170 °C
• Optical Rotation: [α]20/D +62±2°, c = 1% in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (sum of enantiomers, TLC)
• Empirical Formula (Hill Notation): C9H14O6

DETAILS

Sigma Aldrich - 59470

Other Notes
Starting material for the synthesis of an array of compounds modified in the positions 2 and 31,2; synthesis of isopropylidene-L-glyceraldehyde3
Packaging
1, 5 g in glass bottle