N-[(4aR,7R,8R,8aS)-6,8-dihydroxy-2,2-dimethyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]acetamide

• ChemBase ID: 158909
• Molecular Formular: C11H19NO6
• Molecular Mass: 261.27166
• Monoisotopic Mass: 261.12123733
• SMILES: [C@H]1([C@@H](C(O[C@H]2[C@H]1OC(OC2)(C)C)O)NC(=O)C)O
• Canonical SMILES: CC(=O)N[C@@H]1C(O)O[C@H]2[C@H]([C@@H]1O)OC(OC2)(C)C
• InChI: InChI=1S/C11H19NO6/c1-5(13)12-7-8(14)9-6(17-10(7)15)4-16-11(2,3)18-9/h6-10,14-15H,4H2,1-3H3,(H,12,13)/t6-,7-,8-,9-,10?/m1/s1
• InChIKey: KHSNVBRWHNOPEI-WWGUJXLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(4aR,7R,8R,8aS)-6,8-dihydroxy-2,2-dimethyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• IUPAC Traditional name: N-[(4aR,7R,8R,8aS)-6,8-dihydroxy-2,2-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• Synonyms: 2-(Acetylamino)-2-deoxy-4,6-O-(1-methylethylidene)-D-glucose; 2-Acetamido-2-deoxy-4,6-O-isopropylidene-D-glucopyranose

Database IDs

• CAS Number: 50605-09-9
• PubChem SID: 162253044
• PubChem CID: 11459651

CALCULATED PROPERTIES

• Acid pKa: 11.642663
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.5181503
• LogD (pH = 7.4): -1.5181742
• Log P: -1.5181499
• Molar Refractivity: 59.2317 cm^3
• Polarizability: 24.261131 Å^3
• Polar Surface Area: 97.25 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 184-186°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A158350

A useful synthetic intermediate for carbohydrate chemistry.

REFERENCES

• Vypel, H. et al.: J. Med. Chem. 34, 2759 (1991)
• Kuboki, A., et al.: Biosci., Biotechnol., Biochem., 62, 1581 (1991)