(2S,3R,4S,5R,6R)-2-{[(2S,3R,4E)-2-azido-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 161069
• Molecular Formular: C30H59N3O7Si
• Molecular Mass: 601.89086
• Monoisotopic Mass: 601.41222778
• SMILES: O(C[C@@H]([C@@H](/C=C/CCCCCCCCCCCCC)O[Si](C(C)(C)C)(C)C)N=[N+]=[N-])[C@@H]1[C@H]([C@H]([C@H]([C@@H](O1)CO)O)O)O
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](N=[N+]=[N-])CO[C@H]1O[C@@H](CO)[C@@H]([C@@H]([C@@H]1O)O)O)O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C30H59N3O7Si/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-24(40-41(5,6)30(2,3)4)23(32-33-31)22-38-29-28(37)27(36)26(35)25(21-34)39-29/h19-20,23-29,34-37H,7-18,21-22H2,1-6H3/b20-19+/t23-,24+,25+,26-,27-,28+,29-/m0/s1
• InChIKey: KQJXHZRKNUECLZ-ADRJBETJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5R,6R)-2-{[(2S,3R,4E)-2-azido-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3R,4S,5R,6R)-2-{[(2S,3R,4E)-2-azido-3-[(tert-butyldimethylsilyl)oxy]octadec-4-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: (2S,3R,4E)-2-Azido-tert-butyldimethylsilyl-3-hydroxy-4-octadecenyl α-D-Galactopyranoside

Database IDs

• PubChem SID: 162255204
• PubChem CID: 71313598

CALCULATED PROPERTIES

• Acid pKa: 12.210928
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 5.4058
• LogD (pH = 7.4): 5.405793
• Log P: 5.4659
• Molar Refractivity: 158.7884 cm^3
• Polarizability: 64.797966 Å^3
• Polar Surface Area: 138.04 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Yellow Foam

DETAILS

Toronto Research Chemicals - A919935

Intermediate in the preparation of α-Galactosyl-C18-ceramide.