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[ CAS No. 170161-27-0 ] {[proInfo.proName]}

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Chemical Structure| 170161-27-0
Chemical Structure| 170161-27-0
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Product Details of [ 170161-27-0 ]

CAS No. :170161-27-0 MDL No. :MFCD09263315
Formula : C25H48N4O6 Boiling Point : -
Linear Structure Formula :- InChI Key :FIPOUUYFPSMVMX-UHFFFAOYSA-N
M.W : 500.67 Pubchem ID :10940041
Synonyms :

Safety of [ 170161-27-0 ]

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 [ 170161-27-0 ]

* 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 [ 170161-27-0 ]
  • Downstream synthetic route of [ 170161-27-0 ]

[ 170161-27-0 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 170161-27-0 ]
  • [ 110078-46-1 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1996, vol. 133, # 1, p. 65 - 73
  • 2
  • [ 295-37-4 ]
  • [ 24424-99-5 ]
  • [ 170161-27-0 ]
YieldReaction ConditionsOperation in experiment
30% at 0℃; ,4,8-Tris(ter-butoxycarbonyl)-1,4,8,11-tetraazacyclotetradecane (1) was synthesized. Synthesis of 1 was performed by reported methods by Dessolin et al. (J. Dessolin, P. Galea, P. Vlieghe, J. Chermann, J. Kraus, J. Med. Chem. 1999,42, 229-241) with slight modifications. Typically, to a 1gm of cyclam (5.00 mmol, 1 equiv. ) in ice cold CH2C12 (lOOmL) was added to 2.0g of di-tert-butyl dicarbonate (9.00 mmol, 1.8 equiv. ). The solution was stirred overnight. After solvent evaporation, the crude pale yellow oil was {JND0255. DOC;1} - 34 - purified by flash column chromatography (MeOH/CH2Cl2 5: 95). The first fraction collected was the desired tri-boc protected cyclam (1) as the thick colorless oil (0.75g, 30percent yield). MS (electrospray) 523 (M+Na)+
Reference: [1] Molecular Pharmaceutics, 2017, vol. 14, # 5, p. 1395 - 1404
[2] Chemistry (Weinheim an der Bergstrasse, Germany), 2002, vol. 8, # 21, p. 4965 - 4972
[3] Journal of the American Chemical Society, 2006, vol. 128, # 45, p. 14448 - 14449
[4] Chemical Communications, 2018, vol. 54, # 33, p. 4116 - 4119
[5] Bulletin de la Societe Chimique de France, 1996, vol. 133, # 1, p. 65 - 73
[6] European Journal of Inorganic Chemistry, 2017, vol. 2017, # 7, p. 1075 - 1086
[7] Chemical Communications, 2018, vol. 54, # 69, p. 9619 - 9622
[8] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 9, p. 3007 - 3010
[9] European Journal of Inorganic Chemistry, 2006, # 12, p. 2357 - 2363
[10] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 1, p. 71 - 74
[11] Patent: WO2005/117997, 2005, A1, . Location in patent: Page/Page column 34-35
[12] Nucleosides and Nucleotides, 1998, vol. 17, # 5, p. 957 - 968
[13] Tetrahedron Letters, 2002, vol. 43, # 13, p. 2463 - 2466
[14] Synlett, 2004, # 3, p. 453 - 456
[15] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 23, p. 5988 - 5992
[16] Chemical Communications, 2003, # 15, p. 1812 - 1813
[17] ChemMedChem, 2010, vol. 5, # 8, p. 1272 - 1281
[18] Patent: WO2014/153624, 2014, A1, . Location in patent: Page/Page column 42; 43; 44
[19] Biomacromolecules, 2018, vol. 19, # 2, p. 392 - 401
[20] Patent: WO2010/126888, 2010, A1, . Location in patent: Page/Page column 12; 33
  • 3
  • [ 295-37-4 ]
  • [ 24424-99-5 ]
  • [ 1007858-12-9 ]
  • [ 170161-27-0 ]
YieldReaction ConditionsOperation in experiment
35% at 0 - 20℃; Boc Cyclam. [0180] A solution of t-butyl dicarbonate (Boc2O) (2.96 g, 13.1 mmol) in 80 mL of methylene chloride (CH2Cl2) was added dropwise over a period of 2 hours to a solution of cyclam (0.88 g, 4.4 mmol) in CH2Cl2 at 0° C. The mixture was allowed to warm to room temperature and stirred overnight. The mixture was concentrated and purified by chromatography (ethyl acetate (AcOEt)→10:1 AcOEt:methanol (CH3OH)) to give cyclam-Boc4 (0.91 g, 35percent) as a white set foam and cyclam-Boc3 (1.22 g, 56percent) as a light yellow set foam. Tri Boc cyclam: 1H NMR (CDCl3) δ 1.46 (s, 27H), 1.65-1.76 (m, 2H), 2.00-1.80 (m, 2H), 2.62 (bt, J=5.6 Hz, 2H), 2.79 (t, J=4.8 Hz, 2H), 3.31 (t, J=6.4 Hz, 8H), 3.47-3.34 (m, 4H). (see Schickaneder, C.; Heinemann, F. W.; Alsfasser, R. “Copper II Complexes of the Tetraazamacrocyclic Tertiary Amide Ligand Alanyl-Cyclam,” Eur. J. Chem. 2006, 2357-2363)
Reference: [1] Patent: US2014/243397, 2014, A1, . Location in patent: Paragraph 0178-0180
  • 4
  • [ 295-37-4 ]
  • [ 24424-99-5 ]
  • [ 170161-28-1 ]
  • [ 170161-27-0 ]
Reference: [1] Patent: CN105237526, 2016, A, . Location in patent: Paragraph 0021
  • 5
  • [ 295-37-4 ]
  • [ 24424-99-5 ]
  • [ 170161-28-1 ]
  • [ 170161-29-2 ]
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Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 2, p. 229 - 241
[2] Journal of Medicinal Chemistry, 1999, vol. 42, # 2, p. 229 - 241
  • 6
  • [ 295-37-4 ]
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  • [ 170161-28-1 ]
  • [ 170161-29-2 ]
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Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 28, p. 4995 - 4998
[2] Tetrahedron Letters, 1998, vol. 39, # 8, p. 853 - 856
[3] Tetrahedron Letters, 1998, vol. 39, # 8, p. 853 - 856
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