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CAS No. : | 63593-03-3 | MDL No. : | MFCD08704144 |
Formula : | C16H22O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QVXXTLFHRGMIHD-RDBSUJKOSA-N |
M.W : | 310.34 | Pubchem ID : | 10881451 |
Synonyms : |
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.62 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 77.18 |
TPSA : | 77.38 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -8.05 cm/s |
Log Po/w (iLOGP) : | 2.28 |
Log Po/w (XLOGP3) : | 0.2 |
Log Po/w (WLOGP) : | 0.65 |
Log Po/w (MLOGP) : | 0.22 |
Log Po/w (SILICOS-IT) : | 1.59 |
Consensus Log Po/w : | 0.99 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.76 |
Solubility : | 5.37 mg/ml ; 0.0173 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.38 |
Solubility : | 12.8 mg/ml ; 0.0413 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.85 |
Solubility : | 0.439 mg/ml ; 0.00142 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 4.11 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
47% | With sodium hydroxide In tetrahydrofuran; water at 20℃; | Into a 3000-mE round-bottom flask, was placed a solution of 269-4 (100 g, 359.32 mmol, 1.00 eq.) in tetrahydroffiran (500 mE) at RT. Water (500 mE) was added. To the mixture was added a NaOH solution (600 mE, 2 N in water) at 0° C. followed by aq. formaldehyde (240 mE, 37percent). The solution was stirred overnight at RT. The mixture was diluted with EA (1500 mE), washed with sat. NaC1 solution (3x500 |
47% | With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; | Into a 3000-mL round-bottom flask, was placed a solution of 278-4 (100 g, 359.32 mmol, 1.00 eq.) in tetrahydrofuran (500 mL) at RT. Water (500 mL) was added. To the mixture was added a NaOH solution (600 mL, 2 N in water) at 0° C. followed by aq. formaldehyde (240 mL, 37percent). The solution was stirred overnight at RT. The mixture was diluted with EA (1500 mL), washed with sat. NaCl solution (3×500 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by a silica gel column with EA:PE (1:1) to give 278-5 (52.5 g, 47percent) as a white solid. ESI MS m/z: 333 [M+Na]+. |
52.5 g | With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; | Into a 3000-mL round-bottom flask, was placed a solution of 266-4 (100 g, 359.32 mmol, 1.00 eq.) intetrahydrofuran (500 mL) at RT. Water (500 mL) was added. To the mixture was added a NaOH solution(600 mL, 2 N in water) at 0° C. followed by aq. formaldehyde (240 mL, 37percent). The solution was stirredovernight at RT. The mixture was diluted with EA (1500 mL), washed with sat. NaCl solution (3×500 mL),dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude productwas purified by a silica gel column with EA:PE (1:1) to give 266-5 (52.5 g, 47percent) as a white solid. ESI MSm/z: 333 [M+Na]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77 g | With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; for 144 h; | To 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdofuranose (68 g, 0.245 mol) in water (150 mL) and 1,4-dioxane (170 mL) at 0 °C was added formaldehyde (135 mL of a 37percent aqueous solution) followed by sodium hydroxide (665 mL of a 1.0 M aqueous solution, 0.665 mol). The reaction mixture was stirred at room temperature for 6 d, then extracted with ethyl acetate (2 x 1 L). The combined organics were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give 3-O-benzyl-4-(hydroxymethyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranose (77 g) as a yellow oil. |