(2R,3R,4R,5S)-5-(acetyloxy)-4-(benzoyloxy)-2-[(benzoyloxy)methyl]oxolan-3-yl benzoate

• ChemBase ID: 102911
• Molecular Formular: C28H24O9
• Molecular Mass: 504.48476
• Monoisotopic Mass: 504.14203235
• SMILES: O=C(O[C@@H]1O[C@@H]([C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1)COC(=O)c1ccccc1)C
• Canonical SMILES: CC(=O)O[C@@H]1O[C@@H]([C@H]([C@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)COC(=O)c1ccccc1
• InChI: InChI=1S/C28H24O9/c1-18(29)34-28-24(37-27(32)21-15-9-4-10-16-21)23(36-26(31)20-13-7-3-8-14-20)22(35-28)17-33-25(30)19-11-5-2-6-12-19/h2-16,22-24,28H,17H2,1H3/t22-,23-,24-,28-/m1/s1
• InChIKey: GCZABPLTDYVJMP-CBUXHAPBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S)-5-(acetyloxy)-4-(benzoyloxy)-2-[(benzoyloxy)methyl]oxolan-3-yl benzoate; (2S,3R,4R,5R)-2-(acetyloxy)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]oxolan-3-yl benzoate; [(2R,3R,4R,5S)-5-(acetyloxy)-3,4-bis(benzoyloxy)oxolan-2-yl]methyl benzoate
• IUPAC Traditional name: (2R,3R,4R,5S)-5-(acetyloxy)-4-(benzoyloxy)-2-[(benzoyloxy)methyl]oxolan-3-yl benzoate; (2S,3R,4R,5R)-2-(acetyloxy)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]oxolan-3-yl benzoate; [(2R,3R,4R,5S)-5-(acetyloxy)-3,4-bis(benzoyloxy)oxolan-2-yl]methyl benzoate
• Synonyms: 1-Acetyl-2,3,5-tribenzoyl-β-D-ribofuranoside; β-D-Ribofuranose 1-acetate 2,3,5-tribenzoate; 1-O-ACETYL-2,3,5-TRIBENZOYL-β-D-RIBOFURANOSIDE; 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; β-D-Ribofuranose 1-acetate 2,3,5-tribenzoate; beta-D-Ribofuranose 1-Acetate 2,3,5-Tribenzoate; β-D-Ribofuranose 1-acetate 2,3,5-tribenzoate; β-D-Ribofuranose 1-Αcetate 2,3,5-Tribenzoate; 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribose; 2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl Acetate; ABR; NSC 23349; 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 1-ACETYL-2,3,5-TRIBENZOYL-β-D-RIBOFURANOSE; 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 2,3,5-TRI-O-BENZOYL-1-O-ACETYL-β-D-RIBOFURANOSE; 1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖; 1-乙酰氧基-2,3,5-三苯甲酰氧基-1-β-D-呋喃核糖; 1-乙酰基-2,3,5-三苯甲酰基-β-D-呋喃核糖; 1-O-乙酰基-2,3,5-O-三苯甲酰基-β-D-呋喃核糖

Database IDs

• CAS Number: 6974-32-9
• EC Number: 230-220-4
• MDL Number: MFCD00005357
• Beilstein Number: 100243
• PubChem SID: 162091287; 24844890; 24849784
• PubChem CID: 81455

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 5.6248207
• LogD (pH = 7.4): 5.6248207
• Log P: 5.6248207
• Molar Refractivity: 128.5784 cm^3
• Polarizability: 50.93317 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Pyridine
• Apperance: White Solid
• Melting Point: 128-130 °C; 128-130 °C(lit.); 128-130°C; 128-130°C
• Optical Rotation: [α]20/D +24.3°, c = 1 in pyridine; [α]20/D +44±1°, c = 0.5% in chloroform

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (TLC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C28H24O9

DETAILS

MP Biomedicals - 02105455

Crystalline
An important intermediate in the chemical synthesis of ribonucleosides.

MP Biomedicals - 05206427

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 159018

Application
Starting material for nucleoside synthesis.
Packaging
1, 10 g in glass bottle

Sigma Aldrich - 01510

Other Notes
Ribose derivative used for the synthesis of nucleosides1,2,3,4; 1-cyanation with Me3SiC

Toronto Research Chemicals - A189330

An inhibitor of neutrophil-keyhole limpet hemocyanin adhesion. Anti-inflammatory agent.

REFERENCES

• Shappell, S., et al.: J. Immunol., 144, 2702 (1990)
• Ross, L., et al.: J. Biol. Chem., 267, 8537 (1990)
• Granger, D., et al.: J. Leukoc. Biol., 55, 662 (1990)