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

• ChemBase ID: 91993
• Molecular Formular: C16H21NO9S
• Molecular Mass: 403.40424
• Monoisotopic Mass: 403.09370226
• SMILES: O1[C@@H]([C@@H]([C@H]([C@@H]([C@H]1SCC#N)OC(=O)C)OC(=O)C)OC(=O)C)COC(=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-DGADGQDISA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 61145-33-3
• MDL Number: MFCD00057536
• PubChem SID: 162078691
• PubChem CID: 71299582

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

• Melting Point: 95-97°C

Safety Information

• Storage Warning: Irritant/Store at -20°C

DETAILS

Apollo Scientific Ltd - OR8195T

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