N-[(2S,3R,4R,5S,6R)-2-(ethylsulfanyl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 168379
• Molecular Formular: C10H19NO5S
• Molecular Mass: 265.32656
• Monoisotopic Mass: 265.09839371
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)SCC)NC(=O)C)O)O
• Canonical SMILES: CCS[C@@H]1O[C@@H](CO)[C@H]([C@@H]([C@@H]1NC(=O)C)O)O
• InChI: InChI=1S/C10H19NO5S/c1-3-17-10-7(11-5(2)13)9(15)8(14)6(4-12)16-10/h6-10,12,14-15H,3-4H2,1-2H3,(H,11,13)/t6-,7-,8-,9-,10+/m1/s1
• InChIKey: GLDKHCZSFYJVMF-IGORNWKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-2-(ethylsulfanyl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-2-(ethylsulfanyl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: Ethyl 2-(Acetylamino)-2-deoxy-1-thio-β-D-glucopyranoside; Ethyl 2-Acetamido-2-deoxy-β-D-thioglucopyranoside

Database IDs

• CAS Number: 122331-70-8
• PubChem SID: 162262511
• PubChem CID: 10879994

CALCULATED PROPERTIES

• Acid pKa: 12.612356
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.613427
• LogD (pH = 7.4): -1.6134292
• Log P: -1.6134267
• Molar Refractivity: 62.6939 cm^3
• Polarizability: 25.392435 Å^3
• Polar Surface Area: 99.02 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 216-218°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E894750

It is used in the synthesis of modified carbohydrates with glycosidases: stereo- and regiospecific syntheses of lactosamine derivatives and related compounds.

REFERENCES

• Cantacuzene, D., et al.: Carbohydr. Res., 211, 327 (1991)
• Nilsson, K., et al.: Biotechnol. Lett., 17, 717 (1991)