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[ CAS No. 71989-14-5 ] {[proInfo.proName]}

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Chemical Structure| 71989-14-5
Chemical Structure| 71989-14-5
Structure of 71989-14-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 71989-14-5 ]

CAS No. :71989-14-5 MDL No. :MFCD00037131
Formula : C23H25NO6 Boiling Point : -
Linear Structure Formula :- InChI Key :FODJWPHPWBKDON-IBGZPJMESA-N
M.W : 411.45 Pubchem ID :2724635
Synonyms :
4-tert-Butyl N-(fluoren-9-ylmethoxycarbonyl)-L-aspartate;Fmoc-L-Asp(OtBu)-OH

Calculated chemistry of [ 71989-14-5 ]

Physicochemical Properties

Num. heavy atoms : 30
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.35
Num. rotatable bonds : 10
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 110.53
TPSA : 101.93 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.84
Log Po/w (XLOGP3) : 3.5
Log Po/w (WLOGP) : 3.71
Log Po/w (MLOGP) : 2.56
Log Po/w (SILICOS-IT) : 3.32
Consensus Log Po/w : 3.19

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -4.23
Solubility : 0.0241 mg/ml ; 0.0000586 mol/l
Class : Moderately soluble
Log S (Ali) : -5.32
Solubility : 0.00195 mg/ml ; 0.00000475 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.74
Solubility : 0.000749 mg/ml ; 0.00000182 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.07

Safety of [ 71989-14-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 71989-14-5 ]

* 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 [ 71989-14-5 ]
  • Downstream synthetic route of [ 71989-14-5 ]

[ 71989-14-5 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 71989-14-5 ]
  • [ 136083-57-3 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 31, p. 11014 - 11016
[2] Journal of Peptide Science, 2010, vol. 16, # 3, p. 159 - 164
[3] Organic Letters, 2012, vol. 14, # 24, p. 6346 - 6349
  • 2
  • [ 144120-52-5 ]
  • [ 71989-14-5 ]
YieldReaction ConditionsOperation in experiment
62% With [2-(dicyclohexylphosphino)ethyl]trimethylammonium chloride; phenylsilane In tetrahydrofuran; water at 20℃; for 2 h; Inert atmosphere General procedure: A suspension of PdEnCat 30 (Aldrich; 0.4 mmol/g loading, 0.05 equiv) inTHF–H2O (9:1, 5 mL) was bubbled with argon for 10 min.After this time, DCHT (0.15 equiv) and the correspondingallyl ester 1 (1.0 equiv, 70 mg) were added under positivepressure. Finally, PhSiH3 was injected (2.0 equiv), and themixture was allowed to react for 2 h at r.t. under an argonatmosphere. After this time, the reaction was filtered throughCelite and the filtrate was evaporated under reducedpressure. The remaining solid was dissolved with EtOAc (20mL) and washed with H2O (3 × 10 mL) and brine (3 × 10mL). The organic layer was dried (MgSO4) and evaporatedunder vacuum. Purification by solid-phase extraction (C18reverse-phase chromatography, H2O/MeOH) gave purecarboxylic acids 2 (yields shown in Table 1). Purity wasdetermined by HPLC, 1H NMR and 13C NMR analyses. Allthe carboxylic acids are commercially available. Therecorded 1H and 13C NMR spectra of the synthesizedcompounds were consistent with those registered forcommercial samples.
Reference: [1] Synlett, 2014, vol. 25, # 16, p. 2319 - 2322
  • 3
  • [ 82911-69-1 ]
  • [ 3057-74-7 ]
  • [ 71989-14-5 ]
Reference: [1] Synthetic Communications, 2009, vol. 39, # 11, p. 2022 - 2031
[2] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 11, p. 2189 - 2191
  • 4
  • [ 88744-04-1 ]
  • [ 3057-74-7 ]
  • [ 71989-14-5 ]
Reference: [1] Synthesis, 1986, # 4, p. 303 - 305
  • 5
  • [ 3057-74-7 ]
  • [ 99503-04-5 ]
  • [ 71989-14-5 ]
Reference: [1] Synthesis, 1987, # 2, p. 166 - 167
  • 6
  • [ 102774-86-7 ]
  • [ 3057-74-7 ]
  • [ 71989-14-5 ]
Reference: [1] Liebigs Annalen der Chemie, 1988, p. 1095 - 1098
  • 7
  • [ 28920-43-6 ]
  • [ 1334631-58-1 ]
  • [ 71989-14-5 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 23, p. 10575 - 10582
  • 8
  • [ 21715-90-2 ]
  • [ 71989-14-5 ]
Reference: [1] Synthesis, 1987, # 2, p. 166 - 167
  • 9
  • [ 99502-89-3 ]
  • [ 71989-14-5 ]
Reference: [1] Synthesis, 1987, # 2, p. 166 - 167
  • 10
  • [ 56-84-8 ]
  • [ 102774-86-7 ]
  • [ 115-11-7 ]
  • [ 71989-14-5 ]
  • [ 129460-17-9 ]
  • [ 129460-09-9 ]
Reference: [1] Synthesis, 1990, # 7, p. 571 - 572
  • 11
  • [ 147221-34-9 ]
  • [ 71989-14-5 ]
Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 2, p. 323 - 326
  • 12
  • [ 68858-20-8 ]
  • [ 71989-31-6 ]
  • [ 71989-14-5 ]
  • [ 71989-23-6 ]
  • [ 71989-38-3 ]
  • [ 109425-51-6 ]
  • [ 4474-91-3 ]
Reference: [1] European Journal of Inorganic Chemistry, 2016, vol. 2016, # 35, p. 5427 - 5434
  • 13
  • [ 56-84-8 ]
  • [ 102774-86-7 ]
  • [ 115-11-7 ]
  • [ 71989-14-5 ]
  • [ 129460-17-9 ]
  • [ 129460-09-9 ]
Reference: [1] Synthesis, 1990, # 7, p. 571 - 572
  • 14
  • [ 71989-14-5 ]
  • [ 133565-45-4 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 25, p. 8454 - 8462
[2] Organic and Biomolecular Chemistry, 2010, vol. 8, # 21, p. 4855 - 4860
[3] Organic Letters, 2008, vol. 10, # 10, p. 1881 - 1884
[4] Organic and Biomolecular Chemistry, 2011, vol. 9, # 11, p. 4182 - 4187
[5] Journal of the American Chemical Society, 1997, vol. 119, # 7, p. 1556 - 1564
[6] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 5, p. 845 - 851
[7] Journal of Medicinal Chemistry, 2006, vol. 49, # 3, p. 1165 - 1181
[8] Tetrahedron Letters, 1991, vol. 32, # 7, p. 923 - 926
[9] Synlett, 2010, # 5, p. 715 - 720
[10] Journal of the American Chemical Society, 2011, vol. 133, # 6, p. 1946 - 1954
[11] Organic and Biomolecular Chemistry, 2011, vol. 9, # 11, p. 4182 - 4187
[12] Organic Letters, 2015, vol. 17, # 3, p. 640 - 643
  • 15
  • [ 109-02-4 ]
  • [ 71989-14-5 ]
  • [ 543-27-1 ]
  • [ 133565-45-4 ]
Reference: [1] Patent: US6552168, 2003, B1,
  • 16
  • [ 71989-14-5 ]
  • [ 86060-83-5 ]
Reference: [1] Carbohydrate Research, 1988, vol. 174, p. 279 - 290
[2] European Journal of Medicinal Chemistry, 2014, vol. 73, p. 225 - 232
[3] Patent: WO2018/106112, 2018, A1,
  • 17
  • [ 71989-14-5 ]
  • [ 56-84-8 ]
  • [ 3057-74-7 ]
Reference: [1] Amino Acids, 2014, vol. 46, # 2, p. 367 - 374
  • 18
  • [ 71989-14-5 ]
  • [ 144120-53-6 ]
Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 10, p. 1549 - 1552
[2] Tetrahedron Letters, 1993, vol. 34, # 10, p. 1549 - 1552
[3] Tetrahedron Letters, 1992, vol. 33, # 32, p. 4557 - 4560
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7648 - 7662
[5] Patent: US2014/39153, 2014, A1,
  • 19
  • [ 71989-14-5 ]
  • [ 108-24-7 ]
  • [ 117833-18-8 ]
Reference: [1] Patent: WO2014/56923, 2014, A1, . Location in patent: Page/Page column 146; 147
  • 20
  • [ 71989-14-5 ]
  • [ 161529-14-2 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 52, p. 13762 - 13766
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 3, p. 1165 - 1181
[3] Chemical Communications, 2010, vol. 46, # 42, p. 8020 - 8022
[4] Patent: WO2010/65865, 2010, A2, . Location in patent: Page/Page column 287
[5] Patent: WO2014/28381, 2014, A1, . Location in patent: Page/Page column 118
  • 21
  • [ 71989-14-5 ]
  • [ 543-27-1 ]
  • [ 161529-14-2 ]
Reference: [1] Patent: US2002/55631, 2002, A1,
[2] Patent: US2002/86887, 2002, A1,
  • 22
  • [ 71989-14-5 ]
  • [ 209252-17-5 ]
Reference: [1] Synthesis, 1998, # 6, p. 837 - 841
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7648 - 7662
[3] Patent: US2014/39153, 2014, A1,
  • 23
  • [ 71989-14-5 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
[2] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 24
  • [ 71989-14-5 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
[2] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 25
  • [ 71989-14-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Patent: WO2017/30814, 2017, A1,
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