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[ CAS No. 23669-79-6 ] {[proInfo.proName]}

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Chemical Structure| 23669-79-6
Chemical Structure| 23669-79-6
Structure of 23669-79-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 23669-79-6 ]

CAS No. :23669-79-6 MDL No. :MFCD00063410
Formula : C30H30N2O7 Boiling Point : -
Linear Structure Formula :- InChI Key :BYGKUWPLEGHFKX-ZRRKCSAHSA-N
M.W : 530.57 Pubchem ID :90230
Synonyms :
5'-O-DMT-dU

Calculated chemistry of [ 23669-79-6 ]

Physicochemical Properties

Num. heavy atoms : 39
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.27
Num. rotatable bonds : 9
Num. H-bond acceptors : 7.0
Num. H-bond donors : 2.0
Molar Refractivity : 144.17
TPSA : 112.01 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.54
Log Po/w (XLOGP3) : 2.98
Log Po/w (WLOGP) : 2.78
Log Po/w (MLOGP) : 1.37
Log Po/w (SILICOS-IT) : 4.04
Consensus Log Po/w : 2.94

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.87
Solubility : 0.00719 mg/ml ; 0.0000135 mol/l
Class : Moderately soluble
Log S (Ali) : -5.0
Solubility : 0.00536 mg/ml ; 0.0000101 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.01
Solubility : 0.00000517 mg/ml ; 0.0000000098 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.93

Safety of [ 23669-79-6 ]

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 [ 23669-79-6 ]

* 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 [ 23669-79-6 ]
  • Downstream synthetic route of [ 23669-79-6 ]

[ 23669-79-6 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 951-78-0 ]
  • [ 23669-79-6 ]
YieldReaction ConditionsOperation in experiment
89% With lithium carbonate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Heating The unprotected nucleoside (1 eq.) and Li2CO3 (5 eq.) were dried together overnight under vacuum (<0.1 mm Hg). A solution of N,N-diisopropylethylamine (3 eq.) in THF was then added and heated to dissolve the starting materials. The solution was cooled to room temperature and dimethoxytrityl tetrafluoroborate 10 was added in portions of 0.2-0.3 eq., in 30 min intervals. When TLC analysis indicated complete consumption of starting material, or competing formation of di-DMT-protected nucleosides was observed, the additions were stopped and the reaction was allowed to proceed for another 2 h. The mixture was then diluted with CH2Cl2, washed with sat. NaHCO3, H2O and brine, dried over MgSO4, and filtered. Solvents were removed in vacuo and the residue was purified by automated column chromatography on silica gel. Drying under vacuum (<0.1 mm Hg) afforded the DMT-protected products. A detailed representative procedure is given for the preparation of compound 4.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 4, p. 1181 - 1184
  • 2
  • [ 951-78-0 ]
  • [ 40615-36-9 ]
  • [ 23669-79-6 ]
YieldReaction ConditionsOperation in experiment
43 g at 25℃; for 12 h; To a solution of 308-1 (22.80 g, 99.91 mmol) in anhydrous pyridine (200 mE) was added DMTC1 (37.24 g, 109.90 mmol), and the mixture stirred at 25° C. for 12 h. The reaction was quenched with a sat. NH4C1 solution (200 mE), and extracted with EA (3x200 mE). The combined organic layers were washed with brine (2x 100 mE), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA2: 1 to 0:1) to give the desired product (43.00 g, 72.94 mmol) as a yellow foam.
Reference: [1] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 10, p. 1649 - 1658
[2] Organic letters, 2003, vol. 5, # 6, p. 917 - 919
[3] Journal of the American Chemical Society, 2001, vol. 123, # 15, p. 3405 - 3411
[4] Chemical Research in Toxicology, 2006, vol. 19, # 7, p. 968 - 976
[5] Nucleic Acids Research, 2015, vol. 43, # 11, p. 5275 - 5283
[6] Nucleosides, Nucleotides and Nucleic Acids, 2007, vol. 26, # 6-7, p. 709 - 712
[7] ChemMedChem, 2011, vol. 6, # 2, p. 309 - 320
[8] Tetrahedron Letters, 1992, vol. 33, # 1, p. 37 - 40
[9] Chemical & Pharmaceutical Bulletin, 1986, vol. 34, # 5, p. 2044 - 2048
[10] Tetrahedron Letters, 1994, vol. 35, # 29, p. 5221 - 5224
[11] Nucleosides and Nucleotides, 1995, vol. 14, # 3-5, p. 889 - 893
[12] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 14, p. 6824 - 6831
[13] Patent: US2009/264637, 2009, A1, . Location in patent: Page/Page column 29
[14] Bioconjugate Chemistry, 2012, vol. 23, # 3, p. 461 - 471
[15] Photochemical and Photobiological Sciences, 2013, vol. 12, # 8, p. 1366 - 1374
[16] Patent: US2015/366888, 2015, A1, . Location in patent: Paragraph 1309; 1310
[17] Patent: US2015/366887, 2015, A1, . Location in patent: Paragraph 1252-1253
  • 3
  • [ 1254223-76-1 ]
  • [ 23669-79-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 4, p. 1181 - 1184
  • 4
  • [ 40615-36-9 ]
  • [ 23669-79-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 4, p. 1181 - 1184
  • 5
  • [ 40615-35-8 ]
  • [ 23669-79-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 4, p. 1181 - 1184
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