[(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate

• ChemBase ID: 102284
• Molecular Formular: C16H22O11
• Molecular Mass: 390.33928
• Monoisotopic Mass: 390.11621152
• SMILES: O=C(O[C@@H]1O[C@@H]([C@@H](OC(=O)C)[C@H](OC(=O)C)[C@H]1OC(=O)C)COC(=O)C)C
• Canonical SMILES: CC(=O)OC[C@H]1O[C@@H](OC(=O)C)[C@@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15-,16-/m1/s1
• InChIKey: LPTITAGPBXDDGR-IBEHDNSVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate
• Synonyms: beta-D-Glucose pentaacetate; 1,2,3,4,6-Penta-O-acetyl-β-D-glucopyranose; β-D-Glucose pentaacetate; β-D-Glucopyranose 1,2,3,4,6-Pentaacetate; 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl Acetate; NSC 214078; Penta-O-acetyl-β-D-glucose; Pentaacetyl-β-D-glucose; β-D-Glucose Pentaacetate; 1,2,3,4,6-Penta-O-acetyl-β-D-glucopyranose; β-D-GLUCOSE PENTAACETATE; β-D-(+)-Glucose pentaacetate; beta-D-Glucose pentaacetate; 1,2,3,4,6-Pentaacetyl-beta-D-glucose; beta-D-Glucose pentaacetate; 1,2,3,4,6-五-O-乙酰基-β-D-吡喃葡萄糖; β-D-葡萄糖五乙酸酯; β-D-(+)-葡萄糖五乙酸酯

Database IDs

• CAS Number: 604-69-3
• EC Number: 210-074-8
• MDL Number: MFCD00006597
• Beilstein Number: 98851
• PubChem SID: 162089562; 24857226
• PubChem CID: 2724702

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.72691214
• LogD (pH = 7.4): -0.72691214
• Log P: -0.72691214
• Molar Refractivity: 81.6809 cm^3
• Polarizability: 34.419 Å^3
• Polar Surface Area: 140.73 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; chloroform: soluble0.1 g/mL, clear, colorless; Methanol
• Apperance: White Solid
• Melting Point: 128-130°C; 130-132 °C; 130-132 °C(lit.); 130-132°C
• Optical Rotation: [α]20/D +4.2°, c = 1 in chloroform; [α]20/D +4.5±0.5°, c = 5% in chloroform; +5 (c=5 in chloroform)

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC); 98%; 99%
• Grade: for microbiology
• Ignition Residue: ≤0.05%
• Empirical Formula (Hill Notation): C16H22O11

DETAILS

MP Biomedicals - 02100957

Purity: 99%
Crystalline

Sigma Aldrich - 285943

Packaging
100, 500 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 49210

Other Notes
Selective 1-O-deacetylation1; Preparation of 1-β-thioglucoside2; Selective α-1-C-allylation3

Toronto Research Chemicals - G596500

D-Glucose pentaacetate was reported to stimulate insulin release in rat pancreatic islets. Only α-D-glucose pentaacetate caused an immediate increase in insulin output. The β-anomer of D-glucose pentaacetate first transiently inhibited insulin release, th

REFERENCES

• Carpinelli, A., et al.: Mol. Cell Endocrinol., 17, 103 (1980)
• Hellman, B., et al.: Diab. Metab., 20, 123 (1980)
• Malaisse, W., et al.: Int. J. Mol. Med., 2, 331 (1980)
• Sener, A., et al.: Mol. Gen. Metab., 64, 135 (1980)