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

• ChemBase ID: 70278
• Molecular Formular: C13H18O9
• Molecular Mass: 318.27662
• Monoisotopic Mass: 318.09508216
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@H]1O[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C13H18O9/c1-6(14)18-5-10-11(19-7(2)15)12(20-8(3)16)13(22-10)21-9(4)17/h10-13H,5H2,1-4H3/t10-,11-,12-,13-/m1/s1
• InChIKey: IHNHAHWGVLXCCI-FDYHWXHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5S)-3,4,5-tris(acetyloxy)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5S)-3,4,5-tris(acetyloxy)oxolan-2-yl]methyl acetate
• Synonyms: Beta-D-Ribofuranose 1,2,3,5-tetraacetate; 1,2,3,5-Tetra-O-acetyl-β-D-ribofuranose; β-D-Ribofuranose 1,2,3,5-tetraacetate; (2S,3R,4R,5R)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate; 1,2,3,5-Tetra-O-acetyl-beta-D-ribofuranose; beta-D-Ribofuranose 1,2,3,5-tetraacetate; Tetraacetylribose; β-D-Ribofuranose 1,2,3,5-tetra-O-acetate; 1,2,3,5-Tetraacetate β-D-Ribofuranose; β-D-Ribofuranose Tetraacetate; 1,2,3,5-Tetra-O-acetyl-β-D-ribose; 1,2,3,5-Tetraacetyl-β-D-ribofuranose; 1β-D-Tetraacetylribose; NSC 18738; Tetra-O-acetyl-β-D-ribofuranose; Tetraacetyl-β-D-ribofuranose; 1,2,3,5-Tetra-O-acetyl β-D-Ribofuranose; 1,2,3,5-四-O-乙酰基-β-D-呋喃核糖; β-D-呋喃核糖·1,2,3,5-四乙酸酯; β-D-呋喃核糖1,2,3,5-四乙酸酯; 四乙酰基核糖; β-D-呋喃核糖·1,2,3,5-四-O-乙酸酯

Database IDs

• CAS Number: 13035-61-5
• EC Number: 235-898-5
• MDL Number: MFCD00005358
• Beilstein Number: 94078
• PubChem SID: 24849785; 162036001
• PubChem CID: 83064

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.5377026
• LogD (pH = 7.4): -0.5377026
• Log P: -0.5377026
• Molar Refractivity: 66.5669 cm^3
• Polarizability: 28.05088 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 79-82 °C; 80-83°C; 81-83 °C(lit.); 82-84°C
• Optical Rotation: [α]20/D -13±0.5°, c = 2.4% in chloroform; [α]26/D -11.4°, c = 10 in chloroform; -13+/-0.5 (c=2.4 in chloroform)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (TLC); 95+%; 98%; 98+%
• Grade: puriss.
• Empirical Formula (Hill Notation): C13H18O9
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 159026

Application
Starting material for nucleoside synthesis.
Packaging
25 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 86560

Other Notes
Derivative of D-ribose used for ribosylations1,2,3; Selective 1-0-deacetylation4

Toronto Research Chemicals - T283100

Used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.

REFERENCES

• Chwang, T.-L., et al.: J. Med. Chem., 19, 643 (1976)