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[ CAS No. 6564-72-3 ] {[proInfo.proName]}

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Chemical Structure| 6564-72-3
Chemical Structure| 6564-72-3
Structure of 6564-72-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6564-72-3 ]

CAS No. :6564-72-3 MDL No. :MFCD00023849
Formula : C34H36O6 Boiling Point : -
Linear Structure Formula :- InChI Key :OGOMAWHSXRDAKZ-RUOAZZEASA-N
M.W : 540.65 Pubchem ID :11731256
Synonyms :

Calculated chemistry of [ 6564-72-3 ]

Physicochemical Properties

Num. heavy atoms : 40
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.29
Num. rotatable bonds : 13
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 152.6
TPSA : 66.38 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.61
Log Po/w (XLOGP3) : 4.98
Log Po/w (WLOGP) : 5.07
Log Po/w (MLOGP) : 2.86
Log Po/w (SILICOS-IT) : 5.62
Consensus Log Po/w : 4.63

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.92
Solubility : 0.000657 mg/ml ; 0.00000122 mol/l
Class : Moderately soluble
Log S (Ali) : -6.11
Solubility : 0.000417 mg/ml ; 0.000000771 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -10.11
Solubility : 0.0000000422 mg/ml ; 0.0000000001 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 5.59

Safety of [ 6564-72-3 ]

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:

Application In Synthesis of [ 6564-72-3 ]

* 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 [ 6564-72-3 ]
  • Downstream synthetic route of [ 6564-72-3 ]

[ 6564-72-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 6564-72-3 ]
  • [ 13096-62-3 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333 h; Molecular sieve
Stage #2: at 20℃; for 2 h;
EXAMPLE XXI
2,3,4,6-Tetra-O-benzyl-D-glucopyranone
4 g freshly activated molecular sieve 4 Å and 3.3 g N-methylmorpholine-N-oxide are added to a solution of 10.0 g 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in 140 ml dichloromethane.
The solution is stirred for 20 min at ambient temperature, before adding 0.3 g of tetrapropylammonium perruthenate.
After 2 h stirring at ambient temperature the solution is diluted with dichloromethane and filtered through Celite.
The filtrate is washed with aqueous sodium thiosulfate solution and water and then dried over sodium sulfate.
After the solvent is removed the residue is chromatographed through silica gel (cyclohexane/ethyl acetate 4:1).
Yield: 8.2 g (82percent of theory)
Mass spectrum (ESI+): m/z=539 [M+H]+
82%
Stage #1: With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333 h; Molecular sieve
Stage #2: With tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2 h; Molecular sieve
EXAMPLE V
2,3,4,6-Tetra-O-benzyl-D-glucopyranone
To a solution of 10.0 g 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in 140 mL dichloromethane are added 4 g freshly activated molecular sieves 4 Å and 3.3 g N-methylmorpholine-N-oxide.
The solution is stirred for 20 min at ambient temperature, before 0.3 g tetra-n-propylammonium perruthenate are added.
After 2 h stirring at ambient temperature the solution is diluted with dichloromethane and filtered through Celite.
The filtrate is washed with aqueous sodium thiosulfate solution and water and then dried over sodium sulfate.
After the solvent is evaporated, the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1).
Yield: 8.2 g (82percent of theory) Mass spectrum (ESI+): m/z=539 [M+H]+
82%
Stage #1: With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333 h; Molecular sieve 4A
Stage #2: at 20℃; for 2 h;
To a solution of 10.0 g 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in 140 mL dichloromethane are added 4 g freshly activated molecular sieves 4 Å and 3.3 g N-methylmorpholine-N-oxide.
The solution is stirred for 20 min at ambient temperature, before 0.3 g tetra-n-propylammonium perruthenate are added.
After 2 h stirring at ambient temperature the solution is diluted with dichloromethane and filtered through Celite.
The filtrate is washed with aqueous sodium thiosulfate solution and water and then dried over sodium sulfate.
After the solvent is evaporated, the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1).
Yield: 8.2 g (82percent of theory) Mass spectrum (ESI+): m/z=539 [M+H]+
82%
Stage #1: With 4-methylmorpholine N-oxide In dichloromethane at 20℃; for 0.333333 h; Molecular sieve
Stage #2: With tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2 h;
4 g freshly activated molecular sieve 4 Å and 3.3 g N-methylmorpholine-N-oxide are added to a solution of 10.0 g 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in 140 ml dichloromethane.
The solution is stirred for 20 min at ambient temperature, before adding 0.3 g of tetrapropylammonium perruthenate.
After 2 h stirring at ambient temperature the solution is diluted with dichloromethane and filtered through Celite.
The filtrate is washed with aqueous sodium thiosulphate solution and water and then dried over sodium sulphate.
After the solvent has been eliminated the residue is chromatographed through silica gel (cyclohexane/ethyl acetate 4:1).
Yield: 8.2 g (82percent of theory)
Mass spectrum (ESI+): m/z=539 [M+H]+

Reference: [1] Patent: WO2005/92877, 2005, A1, . Location in patent: Page/Page column 63
[2] Patent: US2006/189548, 2006, A1, . Location in patent: Page/Page column 26-27
[3] Patent: US2006/234953, 2006, A1, . Location in patent: Page/Page column 14
[4] Patent: US2007/4648, 2007, A1, . Location in patent: Page/Page column 14
[5] Patent: US2007/27092, 2007, A1, . Location in patent: Page/Page column 26
[6] Tetrahedron, 1994, vol. 50, # 14, p. 4215 - 4224
[7] Chemistry (Weinheim an der Bergstrasse, Germany), 2002, vol. 8, # 8, p. 1872 - 1878
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