(8R,8aR)-2-benzyl-8-[(2,4-dichlorophenoxymethanethioyl)oxy]-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl 4-methylbenzoate

• ChemBase ID: 160645
• Molecular Formular: C29H26Cl2O7S
• Molecular Mass: 589.48354
• Monoisotopic Mass: 588.07762953
• SMILES: [C@H]12[C@@H](C(COC1COC(O2)Cc1ccccc1)OC(=O)c1ccc(cc1)C)OC(=S)Oc1ccc(cc1Cl)Cl
• Canonical SMILES: S=C(Oc1ccc(cc1Cl)Cl)O[C@@H]1C(COC2[C@H]1OC(OC2)Cc1ccccc1)OC(=O)c1ccc(cc1)C
• InChI: InChI=1S/C29H26Cl2O7S/c1-17-7-9-19(10-8-17)28(32)35-24-16-33-23-15-34-25(13-18-5-3-2-4-6-18)37-26(23)27(24)38-29(39)36-22-12-11-20(30)14-21(22)31/h2-12,14,23-27H,13,15-16H2,1H3/t23?,24?,25?,26-,27-/m1/s1
• InChIKey: HUNPVSDJTGKUBR-WBZOCVDESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8R,8aR)-2-benzyl-8-[(2,4-dichlorophenoxymethanethioyl)oxy]-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl 4-methylbenzoate
• IUPAC Traditional name: (8R,8aR)-2-benzyl-8-[(2,4-dichlorophenoxymethanethioyl)oxy]-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl 4-methylbenzoate
• Synonyms: 1,5-Anhydro-4,6-O-benzylidene-3-O-[2,4-dichlorophenyl]thiocarbonyloxy-2-O-p-toluoyl-D-glucitol

Database IDs

• PubChem SID: 162254780
• PubChem CID: 71313411

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 8.481779
• LogD (pH = 7.4): 8.481779
• Log P: 8.481779
• Molar Refractivity: 149.6589 cm^3
• Polarizability: 59.609158 Å^3
• Polar Surface Area: 72.45 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 198-200°C

DETAILS

Toronto Research Chemicals - A637680

An useful synthetic intermediate in the preparation of sugar nucleotides.

REFERENCES

• Verheggen, I, et al.: J. Med. Chem., 36, 2033-2040 (1993)