(1R)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol

• ChemBase ID: 104209
• Molecular Formular: C9H16O6
• Molecular Mass: 220.21974
• Monoisotopic Mass: 220.09468823
• SMILES: O1C(O[C@H]2O[C@H]([C@H](O)CO)[C@H](O)[C@@H]12)(C)C
• Canonical SMILES: OC[C@H]([C@H]1O[C@H]2[C@@H]([C@H]1O)OC(O2)(C)C)O
• InChI: InChI=1S/C9H16O6/c1-9(2)14-7-5(12)6(4(11)3-10)13-8(7)15-9/h4-8,10-12H,3H2,1-2H3/t4-,5+,6-,7-,8-/m1/s1
• InChIKey: BGGCXQKYCBBHAH-OZRXBMAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol
• IUPAC Traditional name: (1R)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol
• Synonyms: 1,2-O-Isopropylidene-alpha-D-glucofuranose; Monoacetone glucose; 1,2-O-ISOPROPYLIDENE-α-D-GLUCOFURANOSE; 1,2-O-Isopropylidene-α-D-glucofuranose; 单丙酮葡萄糖; 1,2-O-异亚丙基-α-D-呋喃葡萄糖

Database IDs

• CAS Number: 18549-40-1
• EC Number: 242-420-9
• MDL Number: MFCD00063244
• Beilstein Number: 82670
• PubChem SID: 24895973; 162091890
• PubChem CID: 87704

CALCULATED PROPERTIES

• Acid pKa: 12.800016
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.2301146
• LogD (pH = 7.4): -1.2301164
• Log P: -1.2301146
• Molar Refractivity: 48.1304 cm^3
• Polarizability: 20.00014 Å^3
• Polar Surface Area: 88.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 158-161 °C; 159-160 °C(lit.)
• Optical Rotation: [α]20/D -11.7±0.5°, c = 2% in H2O; [α]20/D -13°, c = 1 in H2O

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98% (TLC); ≥98.5% (TLC); 95+%; 98%
• Grade: puriss.
• Empirical Formula (Hill Notation): C9H16O6

DETAILS

MP Biomedicals - 02155120

(Monoacetone glucose) Crystalline

Sigma Aldrich - I22900

Packaging
25 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 59439

Other Notes
Partially protected D-glucofuranose, an important chiral building block. It can e.g. be selectively derivatized at the primary 6-OH group, or oxidatively cleaved to a pentodialdose derivative1; Direct transformation to the 5,6-anhydro compound (Mitsunobu reaction)2; Preparation of the 3,5-O-benzylidene derivative3