(3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

• ChemBase ID: 109190
• Molecular Formular: C12H20O6
• Molecular Mass: 260.2836
• Monoisotopic Mass: 260.12598836
• SMILES: CC1(C)OC[C@@H](O1)[C@H]1O[C@@H]2OC(C)(C)O[C@@H]2[C@H]1O
• Canonical SMILES: O[C@H]1[C@H](O[C@H]2[C@@H]1OC(O2)(C)C)[C@H]1COC(O1)(C)C
• InChI: InChI=1S/C12H20O6/c1-11(2)14-5-6(16-11)8-7(13)9-10(15-8)18-12(3,4)17-9/h6-10,13H,5H2,1-4H3/t6-,7+,8-,9-,10-/m1/s1
• InChIKey: KEJGAYKWRDILTF-JDDHQFAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol
• IUPAC Traditional name: (3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• Synonyms: 1,2,4,6-DIACETONE-D-GLUCOSE; 1,2,5,6-diisopropylidene-D-glucose; D-Glucose diacetonide; Diacetone-D-glucose; 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose; 1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranose; 1,2:5,6-Diisopropylidene-D-glucose; Diacetone-D-glucose; 1,2:5,6-Bis-O-(1-methylethylidene)-a-D-Glucofuranose; 1,2,5,6-二异亚丙基-D-葡萄糖; 乙酰丙酮-D-葡萄糖; 二丙酮-D-葡萄糖; 双丙酮葡萄糖; 二丙酮-D-葡萄糖

Database IDs

• CAS Number: 582-52-5
• EC Number: 209-486-0
• MDL Number: MFCD00005544
• Beilstein Number: 84386
• Merck Index: 142965
• PubChem SID: 24894140; 24858968; 162094749
• PubChem CID: 7067560

CALCULATED PROPERTIES

• Acid pKa: 12.956559
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.47231
• LogD (pH = 7.4): 0.4723088
• Log P: 0.47231
• Molar Refractivity: 60.3374 cm^3
• Polarizability: 24.877773 Å^3
• Polar Surface Area: 66.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 107-110°C; 109-113 °C(lit.); 110-111 °C(lit.)
• Optical Rotation: [α]20/D -11.5±1°, c = 5% in ethanol; [α]20/D -18°, c = 1% in H2O; -11 (c=5 in ethanol)

Safety Information

• RTECS: LZ4958000
• German water hazard class: 2
• TSCA Listed: 是
• GHS Hazard statements: H303
• GHS Precautionary statements: P312
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (TLC); 98%; 98+%
• Grade: purum
• Empirical Formula (Hill Notation): C12H20O6

DETAILS

MP Biomedicals - 05210148

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 31460

Other Notes
Important protected derivative of glucose; the 3-OH group can be directly manipulated, the 5,6-O-isopropylidene protection is selectively cleavable; oxidation and reduction of the 3-OH leads to an allofuranose derivative; review1,2

Sigma Aldrich - D7600

Packaging
25 g in poly bottle

REFERENCES

• Chiral auxiliary in a general route to enantiomerically pure sulfoxides: J. Org. Chem., 57, 6789 (1992). For an improved method for methyl p-tolyl sulfoxide, see: Synthesis, 761 (1995).