N-[(2R,3R,4R,5S,6R)-6-[(benzyloxy)methyl]-5-hydroxy-2-methoxy-4-(prop-2-en-1-yloxy)oxan-3-yl]acetamide

• ChemBase ID: 173213
• Molecular Formular: C19H27NO6
• Molecular Mass: 365.42078
• Monoisotopic Mass: 365.18383759
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COCc1ccccc1)OC)NC(=O)C)OCC=C)O
• Canonical SMILES: C=CCO[C@H]1[C@H](O)[C@H](COCc2ccccc2)O[C@H]([C@H]1NC(=O)C)OC
• InChI: InChI=1S/C19H27NO6/c1-4-10-25-18-16(20-13(2)21)19(23-3)26-15(17(18)22)12-24-11-14-8-6-5-7-9-14/h4-9,15-19,22H,1,10-12H2,2-3H3,(H,20,21)/t15-,16-,17-,18-,19-/m1/s1
• InChIKey: SGMRSCAPZVOLHO-FVVUREQNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5S,6R)-6-[(benzyloxy)methyl]-5-hydroxy-2-methoxy-4-(prop-2-en-1-yloxy)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4R,5S,6R)-6-[(benzyloxy)methyl]-5-hydroxy-2-methoxy-4-(prop-2-en-1-yloxy)oxan-3-yl]acetamide
• Synonyms: Methyl 2-(Acetylamino)-2-deoxy-6-O-(phenylmethyl)-3-O-2-propen-1-yl-β-D-glucopyranoside; Methyl 2-(Acetylamino)-2-deoxy-6-O-benzyl-3-O-2-propen-1-yl-β-D-glucopyranoside

Database IDs

• CAS Number: 116981-28-3
• PubChem SID: 164229123
• PubChem CID: 13991479

CALCULATED PROPERTIES

• Acid pKa: 12.440937
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.1645278
• LogD (pH = 7.4): 1.1645244
• Log P: 1.164528
• Molar Refractivity: 95.0536 cm^3
• Polarizability: 37.932076 Å^3
• Polar Surface Area: 86.25 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Off-white Crystals

Safety Information

• Storage Condition: Room Temp

DETAILS

Toronto Research Chemicals - M275240

Used in the preparation of of glycosides and oligosaccharides.

REFERENCES

• Cheng, A. et al.; J. Org. Chem. 73, 7574 (2008)