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[ CAS No. 16652-76-9 ] {[proInfo.proName]}

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Chemical Structure| 16652-76-9
Chemical Structure| 16652-76-9
Structure of 16652-76-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 16652-76-9 ]

CAS No. :16652-76-9 MDL No. :MFCD00038908
Formula : C19H25NO5S Boiling Point : -
Linear Structure Formula :- InChI Key :QWUQVUDPBXFOKF-MERQFXBCSA-N
M.W :379.47 Pubchem ID :11567066
Synonyms :

Calculated chemistry of [ 16652-76-9 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.32
Num. rotatable bonds : 6
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 100.7
TPSA : 115.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.55
Log Po/w (XLOGP3) : 0.82
Log Po/w (WLOGP) : 3.88
Log Po/w (MLOGP) : 2.73
Log Po/w (SILICOS-IT) : 1.95
Consensus Log Po/w : 2.59

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.65
Solubility : 0.84 mg/ml ; 0.00221 mol/l
Class : Soluble
Log S (Ali) : -2.82
Solubility : 0.576 mg/ml ; 0.00152 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.371 mg/ml ; 0.000977 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.33

Safety of [ 16652-76-9 ]

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 [ 16652-76-9 ]

* 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 [ 16652-76-9 ]
  • Downstream synthetic route of [ 16652-76-9 ]

[ 16652-76-9 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 16652-76-9 ]
  • [ 13588-95-9 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 9, p. 2705 - 2707
  • 2
  • [ 72-18-4 ]
  • [ 104-15-4 ]
  • [ 100-51-6 ]
  • [ 16652-76-9 ]
YieldReaction ConditionsOperation in experiment
88% for 4 h; Dean-Stark; Reflux General procedure: The esterifications were carried out on L amino acids withthe exception of phenylglycine, the D enantiomer of whichwas used. A mixture of amino acid (0.05 mol), p-toluenesulfonicacid (0.06 mol), benzyl alcohol (0.25 mol) andcyclohexane (30 mL) was refluxed for 4 h using a Dean-Stark apparatus to separate water that was azeotroped outas it formed. The reaction mixture was cooled to roomtemperature and ethyl acetate (80 mL) was added. Afterstirring for 1 h, the precipitate was collected by filtrationand dried to give the corresponding benzyl ester p-toluenesulfonateas a white solid. According to this procedure,the amino acids 1–6 were converted into the correspondingbenzyl ester p-toluenesulfonates 1a–6a. The benzylationof 7 was accomplished in the same manner but in thepresence of more p-toluenesulfonic acid (0.11 mol) to givethe di-p-toluenesulfonate 7a as a white solid. The p-toluenesulfonate8a separated at the end of the reaction as anoil; instead of adding ethyl acetate, the supernatant wasremoved, the oily phase was washed with cyclohexane andthen poured into dichloromethane/aqueous Na2CO3. Afterremoving the water layer and evaporating dichloromethane,the residue was treated with hydrochloric methanol to give the corresponding hydrochloride as a white solid. Thebenzylation of 9 was prolonged over night and, at the endof the reaction, 9a separated as an oil, which was pouredinto dichloromethane/water. After removing the organiclayer, the water phase was made alkaline with NaHCO3 andextracted with ethyl acetate. The organic extract was concentratedto a small volume and a slight excess of p-toluenesulfonicacid was added to precipitate 9a as a white crystallinesolid.
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 49, p. 6962 - 6964
[2] Journal of the Indian Chemical Society, 2001, vol. 78, # 3, p. 137 - 141
[3] Amino Acids, 2017, vol. 49, # 5, p. 965 - 974
[4] Chirality, 2012, vol. 24, # 2, p. 188 - 192
[5] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 962 - 977
  • 3
  • [ 104-15-4 ]
  • [ 138892-14-5 ]
  • [ 16652-76-9 ]
Reference: [1] Synthesis, 1991, # 11, p. 989 - 993
  • 4
  • [ 4070-48-8 ]
  • [ 16652-76-9 ]
Reference: [1] Synthesis, 1991, # 11, p. 989 - 993
  • 5
  • [ 138892-08-7 ]
  • [ 16652-76-9 ]
Reference: [1] Synthesis, 1991, # 11, p. 989 - 993
  • 6
  • [ 21760-98-5 ]
  • [ 104-15-4 ]
  • [ 16652-76-9 ]
Reference: [1] Letters in Organic Chemistry, 2010, vol. 7, # 1, p. 39 - 44
  • 7
  • [ 16652-76-9 ]
  • [ 28334-73-8 ]
Reference: [1] Helvetica Chimica Acta, 1993, vol. 76, # 1, p. 563 - 595
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