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CAS No. : | 3520-64-7 | MDL No. : | MFCD31814463 |
Formula : | C21H26O10 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OBNBHYQEYRONSE-XDWAVFMPSA-N |
M.W : | 438.43 | Pubchem ID : | 13325754 |
Synonyms : |
|
Num. heavy atoms : | 31 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.52 |
Num. rotatable bonds : | 11 |
Num. H-bond acceptors : | 10.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 104.5 |
TPSA : | 123.66 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -7.01 cm/s |
Log Po/w (iLOGP) : | 3.58 |
Log Po/w (XLOGP3) : | 2.77 |
Log Po/w (WLOGP) : | 1.46 |
Log Po/w (MLOGP) : | 1.02 |
Log Po/w (SILICOS-IT) : | 1.72 |
Consensus Log Po/w : | 2.11 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.72 |
Solubility : | 0.0834 mg/ml ; 0.00019 mol/l |
Class : | Soluble |
Log S (Ali) : | -5.02 |
Solubility : | 0.00416 mg/ml ; 0.0000095 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.1 |
Solubility : | 0.349 mg/ml ; 0.000796 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.84 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Ag2CO3 (2 equiv) and BTEACl (2 equiv) were stirred in the RTIL (1.5 g) at room temperature for 1 h followed by addition of phenol (1.5 equiv). After 20 min at 25 C, 1a (0.7 mmol) was added to the reaction mixture |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3% | With silver carbonate; In 1,2-dichloro-ethane; at 40℃; for 1h; | General procedure: Under nitrogen atmosphere, 1,2-dichloroethane (2 mL) was added to a flask containing 2,3,4,6-tetra-O-acetyl-a-D-galactopyranosyl bromide (103 mg, 0.25 mmol) and phenol derivative (0.75 mmol). Silver carbonate (0.50 mmol) was then added, and the solution was stirred for specified time and temperature, monitoring by TLC and LCMS. Upon completion, the reaction was cooled, filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography with hexane/ethyl acetate combinations as eluent, to give the glycosylation product. Following glycosylation protocol "B", described in Example 1, acetobromogalactose tetraacetate (0.100 g, 0.24 mmol) was coupled with guaiacol (0.090 g, 0.73 mmol) in 1,2-dichloroethane (40C for 1 h), to give glycosylation product, 2-cyanophenyl 2,3,4,6-tetra-0-acetyl^-D- galactopyranoside, in 16% yield; ESI-MS [M+Na]+ calcd for C2iH260iiNa+ 477.14, found 477.3. The acetates were subsequently removed via the deprotection protocol "A" described in Example 1 to give the title compound (5beta) in quantitative yield. Analytical data for (5beta): IH NMR (400 MHz, Methanol-d4) delta ppm 7.18 (d, J=7.4 Hz, IH), 6.97 - 7.01 (m, 2H), 6.86 - 6.91 (m, IH), 4.85 (d, IH), 3.89 (d, J=3.5 Hz, IH), 3.85 (s, 3H), 3.81 - 3.84 (m, IH), 3.76 (d, J=2.0 Hz, IH), 3.74 (s, IH), 3.62 - 3.66 (m, IH), 3.58 (dd, J=9.8, 3.5 Hz, IH); ESI-MS [M+Na]+ calcd for Ci3Hi807Na+ 309.10, found 309.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In tetrachloromethane; | Preparation: 1.4 g (3.2 mmoles) of 4-methylphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranoside (71) and 0.46 g (1.6 mmole) of 1,3-dibromo 5,5-dimethylhydantoine are added in 100 ml of carbone tetrachloride, and the mixture est refluxed under irradiation with light (1 000 W) for 15 minutes. After cooling, the reaction medium is filtered and the filtrate is then evaporated to dryness. 3.5 g of 4-bromomethylphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranoside (72) are isolated by crystallization from methanol (yield=76%). Compound 72: C21 H25 O10 Br, M=517; F=105 C. (MeOH); [alpha]D20 =+168 (c 1, CHCl3); IR (KBr) cm-1: 1747 (nuC=O ester), 1222 (omegaCH2 Br); 1 H NMR (270 MHz, CDCl3) delta ppm: 1.97 (s, 3H), 2.08 (s, 3H), 2.10 (s, 3H), 2.21 (s, 3H), 4.05 (dd, J=11 et 7 Hz, 1H), 4.13 (dd, J=11 et 6 Hz, 1H), 4.18 (t, J=7 Hz, 1H), 4.52 (s, 2H), 5.28 (dd, J=11 et 4 Hz, 1H), 5.52 (d, J=3 Hz, 1H), 5.58 (dd, J=11 et 3 Hz, 1H), 5.79 (d, J=4 Hz, 1H), 7.04 (d, J=9 Hz, 2H), 7.35 (d, J=9 Hz, 2H). SM (DIC/NH3) m/z: 534/536 (M+NH4)+. |