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Volumn , Issue 14, 2007, Pages 2201-2204

Highly efficient synthesis and inclusion properties of star-shaped amphiphilic derivatives of cholic acid

Author keywords

Conjugation; Host guest systems; Oligomerization; Steroids; Supermolecular chemistry

Indexed keywords

ACYL AZIDE; AMPHOPHILE; AZIDE; CHOLIC ACID DERIVATIVE; COPPER; FLUORESCENT DYE; UNCLASSIFIED DRUG;

EID: 34548753913     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984909     Document Type: Article
Times cited : (13)

References (41)
  • 18
    • 33748461404 scopus 로고    scopus 로고
    • Special issue: Fibrillar Networks as Advanced Materials: Babu, P.; Sangeetha, N. M.; Maitra, U. Macromol. Symp. 2006, 241, 60.
    • (a) Special issue: Fibrillar Networks as Advanced Materials: Babu, P.; Sangeetha, N. M.; Maitra, U. Macromol. Symp. 2006, 241, 60.
  • 27
    • 34548755031 scopus 로고    scopus 로고
    • Preparation of Trimer 6 (Similar for Tetramer 7) A solution of cholic acid 2-azidoethyl ester (5, 1 mmol, 476 mg, trialkyne (0.33 mmol, 83 mg, DIPEA (0.5 mL, PPh3 (0.1 mmol, 26 mg, and CuBr (15 mg, 0.1 equiv) in 10 mL DMF was stirred at r.t. for 48 h. Then 50 mL of H2O was added to precipitate out the sticky crude product which was dried under vacuum at 40°C. Column chromatography of the crude product on silica gel with an eluent of 4:1 EtOAc-MeOH gave 240 mg of a light yellow solid 6 in 44% yield. 1H NMR (400 MHz, CD3OD, δ, 8.06 (3 H, s, 4.71 (6 H, t, J, 4.5 Hz, 4.57 (6 H, s, 4.51 (6 H, t, J, 4.0 Hz, 3.95 (3 H, s, 3.81 (3 H, s, 3.48 (8 H, s, 3.59 (2 H, s, 3.50 (6 H, s, 3.39 (3 H, m, 2.18-2.41 (12 H, m, 1.20-2.00 (69 H, m, 1.20-2.37 (63 H, m, 0.97 (9 H. d, J, 6.4 Hz, 0.93 (9 H, s, 0.70 (9 H, s, 13C NMR 100 MHz, CD3OD, δ, 12.1, 16.7, 22.2, 23.3
    • +: 2198.4170.
  • 29
    • 34548710730 scopus 로고    scopus 로고
    • Preparation of Trimer 9 3β-Azido-cholic acid (8, 0.6 mmol, 270 mg, trialkyne (0.2 mmol, 51.8 mg, CuSO4 (0.03 mmol, 7.5 mg) and sodium ascorbate (0.12 mmol, 24 mg) were suspended in a 2:1 mixture (20 mL) of H2O and t-BuOH, and the mixture was stirred at 90°C for 48 h. The crude product precipitated at r.t. by adding 50 mL of H 2O, and was collected by centrifugation. The residue was purified by column chromatography on silica gel with a 5:1:1 mixture of EtOAc-MeOH-AcOH as eluent to give a light yellow solid (175 mg, 54, 1H NMR (400 MHz, CD3OD, δ, 8.14 (3 H, s, 4.70 (6 H, s, 4.59 (6 H, s, 4.00 (3 H, s, 3.85 (3 H, s, 3.56 (2 H, s, 3.48 (6 H, s, 3.50 (6 H, s, 3.07 (3 H, t, J, 13.1 Hz, 1.20-2.00 (69 H, m, 1.20-2.42 (69 H, m, 1.04 (9 H, d, J, 6.6 Hz, 0.89 (9 H, s, 0.74 (9 H, s, 13C NMR 100 MHz, CD3OD, δ, 12.0, 16.6, 19.5, 22.5, 23.2, 24
    • +: 1551.0133.
  • 36
    • 34548727990 scopus 로고    scopus 로고
    • Curtius Reaction to Prepare Trimer 14 A pressure-resistant vessel equipped with a Teflon screw cap was used as the reactor. A solution of choloyl azide 10 (2.3 mmol, 1 g) in 20 mL THF was tightly sealed and stirred at 140°C for 30 min and cooled down to r.t. Triaminoethylamine (0.77 mmol, 0.11 g) was added into the solution and then stirred at 120°C overnight. Then THF was evaporated under vacuum. The residue was purified by column chromatography on silica gel with a 1:1 mixture of EtOAc-MeOH as eluent to yield 900 mg (80, of a white solid product 14. 1H NMR (400 MHz, CD3OD, δ, 3.98 (3 H, s, 3.81 (3 H, s, 3.39 (3 H, m, 3.23 (3 H, m, 3.17 (6 H, t, J, 5.5 Hz, 3.10 (3 H, m, 2.58 (6 H, t, J, 5.6 Hz, 2.18-2.41 (6 H, m, 1.12-2.41 (63 H, m, 1.06 (9 H, d, J, 6.6 Hz, 0.94 (9 H, s, 0.74 (9 H, s, 13C NMR 100 MHz, CD3OD, δ, 12.1, 17.1, 22.2, 23.3, 26.9, 27.9, 28.6, 30.2, 3
    • +: 1754.2938.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.