(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyloxan-2-ol

• ChemBase ID: 141464
• Molecular Formular: C27H30O5
• Molecular Mass: 434.5241
• Monoisotopic Mass: 434.20932406
• SMILES: C[C@H]1[C@H]([C@H]([C@@H](C(O1)O)OCc1ccccc1)OCc1ccccc1)OCc1ccccc1
• Canonical SMILES: C[C@@H]1OC(O)[C@H]([C@@H]([C@@H]1OCc1ccccc1)OCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C27H30O5/c1-20-24(29-17-21-11-5-2-6-12-21)25(30-18-22-13-7-3-8-14-22)26(27(28)32-20)31-19-23-15-9-4-10-16-23/h2-16,20,24-28H,17-19H2,1H3/t20-,24+,25+,26-,27?/m0/s1
• InChIKey: YRAQXZMHYZXWBZ-OGPNLZSQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyloxan-2-ol
• IUPAC Traditional name: (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyloxan-2-ol
• Synonyms: 2,3,4-Tri-O-benzyl-L-fucopyranose; 6-Deoxy-2,3,4-tri-O-(phenylmethyl)-L-galactose; 2,3,4,-Tri-O-benzyl-L-fucopyranose; 2,3,4-三-O-苄基-L-岩藻吡喃糖

Database IDs

• CAS Number: 60431-34-7
• MDL Number: MFCD00153596
• PubChem SID: 162235698
• PubChem CID: 2734155

CALCULATED PROPERTIES

• Acid pKa: 11.345758
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 5.217169
• LogD (pH = 7.4): 5.2171206
• Log P: 5.21717
• Molar Refractivity: 122.4711 cm^3
• Polarizability: 48.740284 Å^3
• Polar Surface Area: 57.15 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White to Off-White Solid
• Melting Point: 89-91°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Store in freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C27H30O5

DETAILS

Sigma Aldrich - 670685

Packaging
1 g in poly tube
5 g in poly bottle

Toronto Research Chemicals - T768000

An intermediate used for the preparation of selectin blockers and other oligosaccharides

REFERENCES

• Susaki, H., et al.: Chem. Pharm. Bull., 42, 1917 (1994)
• Kiyoi, T., et al.: Bioorg. Med. Chem. Lett., 8, 2845 (1994)