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

• ChemBase ID: 104775
• 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-LYYZXLFJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4S,5R,6S)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4S,5R,6S)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl]methyl acetate
• Synonyms: 1,2,3,4,6-Penta-O-acetyl-β-D-galactopyranose; Penta-O-acetyl-β-D-galactopyranose; β-D-Galactose pentaacetate; penta-O-acetyl-β-D-galactopyranose; β-D-GALACTOSE PENTAACETATE; 1,2,3,4,6-Pentaacetyl-beta-D-galactose; beta-D-Galactose pentaacetate; 1,2,3,4,6-五-O-乙酰基-β-D-吡喃半乳糖; 五-O-乙酰基-β-D-吡喃半乳糖; β-D-半乳糖五乙酸酯

Database IDs

• CAS Number: 4163-60-4
• EC Number: 224-008-0
• MDL Number: MFCD00063259
• Beilstein Number: 98853
• PubChem SID: 24848130; 24871841; 162092306
• PubChem CID: 94752

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: methanol: soluble50 mg/mL, clear
• Melting Point: 139-144 °C; 142-146°C; 143-144 °C(lit.)
• Optical Rotation: [α]20/D +23±1°, c = 1% in chloroform; [α]20/D +8.6°, c = 1.5% in chloroform; [α]24/D +23°, c = 1 in chloroform; +24 (c=4 in chloroform)

Safety Information

• Storage Condition: 0°C
• German water hazard class: 1
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (TLC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C16H22O11

DETAILS

MP Biomedicals - 02157180

Prepared from galactose
containing 0.5-5.0% glucose
Crystalline

Sigma Aldrich - 134031

Packaging
25, 100 g in glass bottle

Sigma Aldrich - 48270

Other Notes
Selective 1-O-deacetylation1; Selective β-1-C-allylation2; Stereoselective β-thioglycosidation3

REFERENCES

• Regioselective 1-O-deacylation can be effected with ammonia in acetonitrile at ambient temperature: Synthesis, 1121 (1985).