[(2R,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[(cyanomethyl)sulfanyl]oxan-2-yl]methyl acetate

• ChemBase ID: 165117
• Molecular Formular: C16H21NO9S
• Molecular Mass: 403.40424
• Monoisotopic Mass: 403.09370226
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)SCC#N)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: N#CCS[C@@H]1O[C@@H](COC(=O)C)[C@@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C16H21NO9S/c1-8(18)22-7-12-13(23-9(2)19)14(24-10(3)20)15(25-11(4)21)16(26-12)27-6-5-17/h12-16H,6-7H2,1-4H3/t12-,13+,14+,15-,16+/m1/s1
• InChIKey: ZNQCXCWNORCJGV-CWVYHPPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[(cyanomethyl)sulfanyl]oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[(cyanomethyl)sulfanyl]oxan-2-yl]methyl acetate
• Synonyms: [(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)thio]acetonitrile; Cyanomethyl 2,3,4,6-Tetra-O-acetyl-1-thio-β-D-galactopyranoside

Database IDs

• CAS Number: 61145-33-3
• PubChem SID: 162259250
• PubChem CID: 18634526

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.58932155
• LogD (pH = 7.4): -0.58932155
• Log P: -0.58932155
• Molar Refractivity: 88.6123 cm^3
• Polarizability: 36.476467 Å^3
• Polar Surface Area: 138.22 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ether; Ethyl Acetate; Methanol
• Apperance: White Solid with a Pink Tinge
• Melting Point: 95-97°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C981950

The nitrile of the cyanomethyl group can be converted to a methyl imidate group by treatment with sodium methoxide or HCl which can be used to attach the sugar to a protein.

REFERENCES

• Lee, Y-C, et al.: Biochemistry, 15, 18, 3956 (1976)
• Lee, Y-C, et al.: Biochemistry, 19, 4899 (1980)