[(2R,3R,4R,5R)-3,4-bis(benzoyloxy)-5-isothiocyanatooxolan-2-yl]methyl benzoate

• ChemBase ID: 152869
• Molecular Formular: C27H21NO7S
• Molecular Mass: 503.52314
• Monoisotopic Mass: 503.10387302
• SMILES: c1ccc(cc1)C(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N=C=S)OC(=O)c1ccccc1)OC(=O)c1ccccc1
• Canonical SMILES: S=C=N[C@@H]1O[C@@H]([C@H]([C@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)COC(=O)c1ccccc1
• InChI: InChI=1S/C27H21NO7S/c29-25(18-10-4-1-5-11-18)32-16-21-22(34-26(30)19-12-6-2-7-13-19)23(24(33-21)28-17-36)35-27(31)20-14-8-3-9-15-20/h1-15,21-24H,16H2/t21-,22-,23-,24-/m1/s1
• InChIKey: AWVSFHIUQVIIOW-MOUTVQLLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R)-3,4-bis(benzoyloxy)-5-isothiocyanatooxolan-2-yl]methyl benzoate
• IUPAC Traditional name: [(2R,3R,4R,5R)-3,4-bis(benzoyloxy)-5-isothiocyanatooxolan-2-yl]methyl benzoate
• Synonyms: β-D-ribofuranosyl isothiocyanate tribenzoate; 2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl isothiocyanate; β-D-呋喃核糖基异硫氰酸三苯甲酸酯; 2,3,5-三-O-苯甲酰基-β-D-呋喃核糖异硫氰酸酯

Database IDs

• CAS Number: 58214-53-2
• MDL Number: MFCD03791088
• Beilstein Number: 1275438
• PubChem SID: 24885197; 162247012
• PubChem CID: 13305671

CALCULATED PROPERTIES

• Acid pKa: 15.04103
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 6.7719226
• LogD (pH = 7.4): 6.7719226
• Log P: 6.7719226
• Molar Refractivity: 132.4947 cm^3
• Polarizability: 52.16104 Å^3
• Polar Surface Area: 100.49 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0%
• Empirical Formula (Hill Notation): C27H21NO7S

DETAILS

Sigma Aldrich - 67410

Other Notes
Building block for the synthesis of nucleosides1
Packaging
1 g in poly tube