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[ CAS No. 63593-03-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 63593-03-3
Chemical Structure| 63593-03-3
Structure of 63593-03-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 63593-03-3 ]

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 :

Calculated chemistry of [ 63593-03-3 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.11

Safety of [ 63593-03-3 ]

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:

Application In Synthesis of [ 63593-03-3 ]

* 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.

  • Upstream synthesis route of [ 63593-03-3 ]
  • Downstream synthetic route of [ 63593-03-3 ]

[ 63593-03-3 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 50-00-0 ]
  • [ 63593-02-2 ]
  • [ 63593-03-3 ]
YieldReaction ConditionsOperation 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]+
Reference: [1] Tetrahedron, 2002, vol. 58, # 26, p. 5335 - 5345
[2] Patent: US2015/366888, 2015, A1, . Location in patent: Paragraph 1083; 1087
[3] Patent: US2015/366887, 2015, A1, . Location in patent: Paragraph 1015; 1019
[4] Patent: US2015/105341, 2015, A1, . Location in patent: Paragraph 1148
  • 2
  • [ 50-00-0 ]
  • [ 63593-03-3 ]
YieldReaction ConditionsOperation 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.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2699 - 2702
  • 3
  • [ 620630-82-2 ]
  • [ 63593-03-3 ]
Reference: [1] Patent: US2007/249049, 2007, A1, . Location in patent: Page/Page column 14-15
[2] Patent: US2015/105341, 2015, A1,
[3] Patent: US2015/366887, 2015, A1,
[4] Patent: US2015/366888, 2015, A1,
  • 4
  • [ 100-39-0 ]
  • [ 63593-03-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2699 - 2702
[2] Patent: US2015/105341, 2015, A1,
[3] Patent: US2015/366887, 2015, A1,
[4] Patent: US2015/366888, 2015, A1,
  • 5
  • [ 57099-04-4 ]
  • [ 63593-03-3 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 26, p. 5335 - 5345
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2699 - 2702
  • 6
  • [ 22331-21-1 ]
  • [ 63593-03-3 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 26, p. 5335 - 5345
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2699 - 2702
  • 7
  • [ 1013943-40-2 ]
  • [ 63593-03-3 ]
Reference: [1] Patent: US2015/105341, 2015, A1,
[2] Patent: US2015/366887, 2015, A1,
[3] Patent: US2015/366888, 2015, A1,
  • 8
  • [ 2595-05-3 ]
  • [ 63593-03-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2699 - 2702
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