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

• ChemBase ID: 104016
• Molecular Formular: C26H22O8
• Molecular Mass: 462.44808
• Monoisotopic Mass: 462.13146766
• SMILES: O=C(O[C@H]1O[C@@H]([C@@H](OC(=O)c2ccccc2)[C@H]1O)COC(=O)c1ccccc1)c1ccccc1
• Canonical SMILES: O[C@H]1[C@H](O[C@@H]([C@H]1OC(=O)c1ccccc1)COC(=O)c1ccccc1)OC(=O)c1ccccc1
• InChI: InChI=1S/C26H22O8/c27-21-22(33-24(29)18-12-6-2-7-13-18)20(16-31-23(28)17-10-4-1-5-11-17)32-26(21)34-25(30)19-14-8-3-9-15-19/h1-15,20-22,26-27H,16H2/t20-,21-,22-,26-/m1/s1
• InChIKey: HUHVPBKTTFVAQF-PIXQIBFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-3-hydroxyoxolan-2-yl benzoate; [(2R,3S,4R,5R)-3,5-bis(benzoyloxy)-4-hydroxyoxolan-2-yl]methyl benzoate; (2R,3S,4R,5R)-5-(benzoyloxy)-2-[(benzoyloxy)methyl]-4-hydroxyoxolan-3-yl benzoate
• IUPAC Traditional name: (2R,3R,4S,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-3-hydroxyoxolan-2-yl benzoate; [(2R,3S,4R,5R)-3,5-bis(benzoyloxy)-4-hydroxyoxolan-2-yl]methyl benzoate; (2R,3S,4R,5R)-5-(benzoyloxy)-2-[(benzoyloxy)methyl]-4-hydroxyoxolan-3-yl benzoate
• Synonyms: alpha-D-Ribofuranose 1,3,5-tribenzoate; 1,3,5-Tri-O-benzoyl-alpha-D-ribofuranose; 1,3,5-Tri-O-benzoyl-α-D-ribofuranose; α-D-Ribofuranose 1,3,5-tribenzoate; α-D-Ribofuranose 1,3,5-tribenzoate; 1,3,5-TRI-O-BENZOYL-α-D-RIBOFURANOSE; 1,3,5-三-O-苯甲酰-α-D-呋喃核糖; α-D-呋喃核糖 1,3,5-三苯甲酯

Database IDs

• CAS Number: 22224-41-5
• MDL Number: MFCD00080818
• Beilstein Number: 98446
• PubChem SID: 24889390; 24864261; 162090993
• PubChem CID: 11005061

CALCULATED PROPERTIES

• Acid pKa: 12.318027
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 5.1836953
• LogD (pH = 7.4): 5.18369
• Log P: 5.1836953
• Molar Refractivity: 119.4269 cm^3
• Polarizability: 47.08571 Å^3
• Polar Surface Area: 108.36 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 125-129 °C(lit.); 125-129°C
• Optical Rotation: [α]20/D +85.0°, c = 1 in chloroform; [α]20/D +86±2°, c = 1% in chloroform; +85 (c=1 in chloroform)

Safety Information

• Storage Condition: 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: ≥97.0% (TLC); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C26H22O8

DETAILS

Sigma Aldrich - 389080

Packaging
5 g in glass bottle
Application
Starting material for nucleosides.1,2

Sigma Aldrich - 90650

Other Notes
Building block for preparing 2′-deoxy and 2′-O-substituted nucleosides1,2,3