(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-(ethylsulfanyl)-6-methyloxane

• ChemBase ID: 168778
• Molecular Formular: C29H34O4S
• Molecular Mass: 478.64286
• Monoisotopic Mass: 478.21778057
• SMILES: [C@@H]1([C@H]([C@@H]([C@@H](C(O1)SCC)OCc1ccccc1)OCc1ccccc1)OCc1ccccc1)C
• Canonical SMILES: CCSC1O[C@@H](C)[C@H]([C@@H]([C@@H]1OCc1ccccc1)OCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C29H34O4S/c1-3-34-29-28(32-21-25-17-11-6-12-18-25)27(31-20-24-15-9-5-10-16-24)26(22(2)33-29)30-19-23-13-7-4-8-14-23/h4-18,22,26-29H,3,19-21H2,1-2H3/t22-,26+,27+,28-,29?/m0/s1
• InChIKey: RZVKVTBAQRMTEH-JAGXECETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-(ethylsulfanyl)-6-methyloxane
• IUPAC Traditional name: (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-(ethylsulfanyl)-6-methyloxane
• Synonyms: Ethyl 6-Deoxy-2,3,4-tris-O-(phenylmethyl)-1-thio-L-galactopyranoside; Ethyl 2,3,4-Tri-O-benzyl-1-thio-α,β-L-fucopyranoside

Database IDs

• CAS Number: 169532-17-6
• PubChem SID: 162262910
• PubChem CID: 11081316

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 6.8243175
• LogD (pH = 7.4): 6.8243175
• Log P: 6.8243175
• Molar Refractivity: 138.1403 cm^3
• Polarizability: 54.891373 Å^3
• Polar Surface Area: 36.92 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol

DETAILS

Toronto Research Chemicals - E927500

A useful reagent for the synthesis of oligosaccharides containing L-fucose.

REFERENCES

• Peter, T., et al.: Liebigs Ann. Chem., 237 (1991)
• Thoma, G., et al.: Bioorg. Med. Chem. Lett., 11, 923 (1991)