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[ CAS No. 4546-72-9 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 4546-72-9
Chemical Structure| 4546-72-9
Structure of 4546-72-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4546-72-9 ]

CAS No. :4546-72-9 MDL No. :MFCD00149575
Formula : C17H17N5O4 Boiling Point : -
Linear Structure Formula :- InChI Key :PIXHJAPVPCVZSV-YNEHKIRRSA-N
M.W : 355.35 Pubchem ID :107558
Synonyms :
N-Benzoyldeoxyadenosine;6-N-Benzoyldeoxyadenosine;N-Benzoyl-2'-deoxyadenosine;305808-19-9;4546-72-9

Calculated chemistry of [ 4546-72-9 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.29
Num. rotatable bonds : 5
Num. H-bond acceptors : 7.0
Num. H-bond donors : 3.0
Molar Refractivity : 91.32
TPSA : 122.39 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 0.22
Log Po/w (WLOGP) : 0.2
Log Po/w (MLOGP) : -0.1
Log Po/w (SILICOS-IT) : -0.18
Consensus Log Po/w : 0.41

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.28
Solubility : 1.87 mg/ml ; 0.00526 mol/l
Class : Soluble
Log S (Ali) : -2.35
Solubility : 1.59 mg/ml ; 0.00447 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.23
Solubility : 0.21 mg/ml ; 0.000592 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.83

Safety of [ 4546-72-9 ]

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 [ 4546-72-9 ]

* 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 [ 4546-72-9 ]
  • Downstream synthetic route of [ 4546-72-9 ]

[ 4546-72-9 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 4546-72-9 ]
  • [ 64325-78-6 ]
YieldReaction ConditionsOperation in experiment
58% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 2 h; Inert atmosphere; Schlenk technique General procedure: To a solution of trityl alcohol (0.6 mmol, 1.2 equiv.) in dry CH2Cl2 (5 mL) in a round-bottomed flask was added trifluoroacetic anhydride (0.21 mL, 1.5 mmol, 3 equiv.) at rt under argon from a Schlenk line. A deep red solution was formed immediately (with 1a, the color was slightly lighter). After stirring for 2 h, the mixture was concentrated to dryness on a rotary evaporator under reduced pressure provided by a water aspirator. The flask was reattached to the Schlenk line and flushed with argon. The intermediate trityl cation was re-dissolved in dry THF (5 mL), and added via a cannula to a solution of alcohol substrate (0.5 mmol, 1 equiv.) and DIEA (0.175 mL, 1 mmol, 2 equiv.) in dry THF (5 mL) at rt (5-8) or 0 °C (3, 9-11). After stirring for 2 h (while warming to rt slowly if applicable), the reaction mixture was poured into a separatory funnel containing 5percent NaHCO3 (15 mL), and extracted with EtOAc (10 mL×2). The extracts were dried over anhydrous Na2SO4, filtered, and concentrated.
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 34, p. 3877 - 3880
  • 2
  • [ 40615-36-9 ]
  • [ 4546-72-9 ]
  • [ 64325-78-6 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 48, p. 7319 - 7323
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 3, p. 370 - 371
[3] Liebigs Annalen der Chemie, 1982, # 7, p. 1398 - 1402
[4] Helvetica Chimica Acta, 1982, vol. 65, # 8, p. 2372 - 2393
[5] Nucleosides and Nucleotides, 1997, vol. 16, # 5-6, p. 815 - 820
[6] Nucleosides, Nucleotides and Nucleic Acids, 2004, vol. 23, # 11, p. 1683 - 1705
  • 3
  • [ 40615-36-9 ]
  • [ 4546-72-9 ]
  • [ 64325-78-6 ]
Reference: [1] Patent: EP1253154, 2002, A1, . Location in patent: Example 2
  • 4
  • [ 65-85-0 ]
  • [ 958-09-8 ]
  • [ 4546-72-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 22, p. 5045 - 5048
  • 5
  • [ 64325-78-6 ]
  • [ 4546-72-9 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 44, p. 7755 - 7757
[2] Tetrahedron Letters, 1981, vol. 22, # 38, p. 3761 - 3764
[3] Tetrahedron, 1991, vol. 47, # 14-15, p. 2377 - 2388
[4] Tetrahedron Letters, 1995, vol. 36, # 43, p. 7833 - 7836
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1999, # 11, p. 1477 - 1486
  • 6
  • [ 98-88-4 ]
  • [ 958-09-8 ]
  • [ 4546-72-9 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 11, p. 3274 - 3280
[2] Patent: US4667017, 1987, A,
[3] Journal of the American Chemical Society, 2010, vol. 132, # 11, p. 3862 - 3869
  • 7
  • [ 958-09-8 ]
  • [ 4546-72-9 ]
Reference: [1] Synthetic Communications, 2003, vol. 33, # 7, p. 1233 - 1243
[2] Nucleosides, Nucleotides and Nucleic Acids, 2002, vol. 21, # 4-5, p. 393 - 400
[3] Tetrahedron, 1997, vol. 53, # 33, p. 11317 - 11346
[4] Helvetica Chimica Acta, 1982, vol. 65, # 8, p. 2372 - 2393
[5] Journal of the American Chemical Society, 1982, vol. 104, # 5, p. 1316 - 1319
  • 8
  • [ 64723-02-0 ]
  • [ 4546-72-9 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2002, vol. 21, # 4-5, p. 393 - 400
[2] Helvetica Chimica Acta, 1982, vol. 65, # 8, p. 2372 - 2393
  • 9
  • [ 64911-19-9 ]
  • [ 4546-72-9 ]
Reference: [1] Synthetic Communications, 2003, vol. 33, # 7, p. 1233 - 1243
[2] Journal of the American Chemical Society, 1982, vol. 104, # 5, p. 1316 - 1319
  • 10
  • [ 167872-05-1 ]
  • [ 4546-72-9 ]
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 5, p. 1116 - 1117
  • 11
  • [ 961-07-9 ]
  • [ 4005-49-6 ]
  • [ 4546-72-9 ]
Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2007, vol. 26, # 8-9, p. 905 - 909
  • 12
  • [ 253277-01-9 ]
  • [ 4546-72-9 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 45, p. 7911 - 7915
  • 13
  • [ 440327-41-3 ]
  • [ 4546-72-9 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 13, p. 4513 - 4519
  • 14
  • [ 20187-82-0 ]
  • [ 144924-99-2 ]
  • [ 4546-72-9 ]
Reference: [1] Patent: US5672697, 1997, A,
  • 15
  • [ 91592-96-0 ]
  • [ 4546-72-9 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 33, p. 11317 - 11346
  • 16
  • [ 75759-62-5 ]
  • [ 76-84-6 ]
  • [ 4546-72-9 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 26, p. 2641 - 2644
  • 17
  • [ 75759-62-5 ]
  • [ 4546-72-9 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, p. 2683 - 2686
  • 18
  • [ 1055366-12-5 ]
  • [ 4546-72-9 ]
Reference: [1] Chemistry - A European Journal, 2008, vol. 14, # 21, p. 6490 - 6497
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