References and Notes
1
Mukhopadhyay S.
Maitra U.
Curr. Sci.
2004,
87:
1666
2
Zhu XX.
Nichifor M.
Acc. Chem. Res.
2002,
35:
539
3a
D’Souza LJ.
Maitra U.
J. Org. Chem.
1996,
61:
9494
3b
Shim JH.
Jeong IS.
Lee MH.
Hong HP.
On JH.
Kim KS.
Kim H.-S.
Kim BH.
Cha GS.
Nam H.
Talanta
2004,
63:
61
4a
Zhao Y.
Ryu E.-H.
J. Org. Chem.
2005,
70:
7585
4b
Ryu E.-H.
Zhao Y.
Org. Lett.
2005,
7:
1035
4c
Ryu E.-H.
Zhao Y.
Org. Lett.
2004,
6:
3187
5a
Ariga K.
Nakanishi T.
Hill JP.
Soft Matter
2006,
2:
465
5b
Ariga K.
Nakanishi T.
Hill JP.
Terasaka Y.
Sakai D.
Kikuchi J.-i.
Soft Matter
2005,
1:
132
5c
Ariga K.
Nakanishi T.
Terasaka Y.
Tsuji H.
Sakai D.
Kikuchi J.
Langmuir
2005,
21:
976
6
Janout V.
Lanier M.
Regen SL.
J. Am. Chem. Soc.
1997,
119:
640
7
Janout V.
Di Giorgio C.
Regen SL.
J. Am. Chem. Soc.
2000,
122:
2671
8
Janout V.
Zhang L.-h.
Staina IV.
Di Giorgio C.
Regen SL.
J. Am. Chem. Soc.
2001,
123:
5401
9
Janout V.
Jing B.
Regen SL.
Bioconjugate Chem.
2002,
13:
351
10
Zhao Y.
Zhong Z.
J. Am. Chem. Soc.
2005,
127:
17894
11a
Zhao Y.
Zhong Z.
Org. Lett.
2006,
8:
4715
11b
Zhao Y.
Zhong Z.
J. Am. Chem. Soc.
2006,
128:
9988
12a Special issue: Fibrillar Networks as Advanced Materials: Babu P.
Sangeetha NM.
Maitra U.
Macromol. Symp.
2006,
241:
60
12b
Mukhopadhyay S.
Maitra U.
Ira I.
Krishnamoorthy G.
Schmidt J.
Talmon Y.
J. Am. Chem. Soc.
2004,
126:
15905
13
Aher N.
Pore V.
Synlett
2005,
2155
14a
Bock VD.
Perciaccante R.
Jansen TP.
Hiemstra H.
Van Maarseveen JH.
Org. Lett.
2006,
8:
919
14b
Demko ZP.
Sharpless KB.
Angew. Chem. Int. Ed.
2002,
41:
2113
14c
Kolb HC.
Finn MG.
Sharpless KB.
Angew. Chem. Int. Ed.
2001,
40:
2004
15
Rostovtsev VV.
Green LG.
Fokin VV.
Sharpless KB.
Angew. Chem. Int. Ed.
2002,
41:
2596
16
Calvo-Flores FG.
Isac-Garcia J.
Hernandez-Mateo F.
Perez-Balderas F.
Calvo-Asin JA.
Sanchez-Vaquero E.
Santoyo-Gonzalez F.
Org. Lett.
2000,
2:
2499
17
Hu X.
Zhang Z.
Zhang X.
Li Z.
Zhu XX.
Steroids
2005,
70:
531
18
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, 26.9, 27.7, 28.6, 30.2, 30.8, 31.1, 34.9 (2 C), 35.5, 35.7, 39.5, 40.0, 42.0, 42.3, 45.8, 46.5, 46.9, 49.5, 61.4, 62.5, 64.4, 68.0, 69.2, 71.9, 72.9, 124.4, 174.2. HRMS: m/z calcd for C92H148N9O19 [M + H]+: 1683.0886; found [M + H]+: 1683.0877.
Tetramer 7: 23% yield; mp 140 °C. 1H NMR (400 MHz, CD3OD): δ = 8.01 (4 H, s), 4.71 (8 H, t, J = 5.1 Hz), 4.55 (8 H, s), 4.51 (8 H, t, J = 5.0 Hz), 3.95 (4 H, m), 3.81 (4 H, m), 3.48 (8 H, s), 2.18-2.41 (16 H, m), 1.12-2.41 (80 H, m), 0.97 (12 H, s), 0.93 (12 H, s), 0.70 (12 H, s). 13C NMR (100 MHz, CD3OD): δ = 12.1, 16.7, 22.2, 23.3, 26.9, 27.7, 28.6, 30.2, 30.9, 31.1, 34.9 (2 C), 35.6, 35.7, 39.5, 40.0, 42.0, 42.2, 46.5, 47.0, 49.4, 62.5, 64.5, 68.0, 68.7, 69.0, 71.9, 72.9, 124.7, 174.2. HRMS: m/z calcd for C121H193N12O24 [M + H]+: 2198.4245; found [M + H]+: 2198.4170.
19
Wess G.
Kramer W.
Bartmann W.
Enhsen A.
Glombik H.
Muellner S.
Bock K.
Dries A.
Kleine H.
Schmitt W.
Tetrahedron Lett.
1992,
33:
195
20
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 H2O, and was collected by centrifuga-tion. 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, 24.8, 27.0, 27.7, 28.7, 30.8, 30.9, 31.2, 32.6, 34.1, 35.1, 35.8, 37.5, 40.0, 42.0, 46.6, 47.0, 57.6, 64.3, 67.9, 69.2, 72.9, 113.6, 116.4, 175.0. HRMS: m/z calcd for C86H136N9O16 [M + H]+: 1551.0099; found [M + H]+: 1551.0133.
21
Rodionov VO.
Fokin VV.
Finn MG.
Angew. Chem. Int. Ed.
2005,
44:
2210
22a
Scriven EFTK.
Chem. Rev.
1988,
88:
297
22b
Curtius T.
Ber. Dtsch. Chem. Ges.
1890,
23:
3023
23a
Okaniwa M.
Takeuchi K.
Asai M.
Ueda M.
Macromolecules
2002,
35:
6224
23b
Okaniwa M.
Takeuchi K.
Asai M.
Ueda M.
Macromolecules
2002,
35:
6232
24
Hayes W.
Osborn HMI.
Osborne SD.
Rastall RA.
Romagnoli B.
Tetrahedron
2003,
59:
7983
25
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, 34.1, 34.1, 34.9, 35.5, 36.5, 37.8, 38.4, 39.5, 40.0, 42.0, 42.2, 46.6, 47.5, 55.2, 68.1, 71.9, 73.0, 160.4. HRMS: m/z calcd for C78H133N16O9 [M + H]+: 1438.0435; found [M + H]+: 1438.0453.
Tetramer 15: 54% yield. 1H NMR (400 MHz, CD3OD): δ = 3.99 (4 H, s), 3.81 (4 H, s), 3.39 (4 H, m), 3.19 (8 H, t, J = 7.3 Hz), 2.33 (8 H, s), 2.23-2.37 (8 H, m), 1.12-2.30 (88 H, m), 1.08 (12 H, d, J = 6.3 Hz), 0.94 (12 H, s), 0.74 (12 H, s). 13C NMR (100 MHz, CD3OD): δ = 12.1, 17.1, 22.3, 23.3, 25.5, 26.9, 28.0, 28.6, 30.2, 34.0, 34.9 (2 C), 35.5, 36.6, 37.8, 39.0, 39.5, 40.0, 42.0, 42.2, 46.6, 47.5, 68.1, 71.9, 73.0, 160.2. HRMS: m/z calcd for C101H173N8O16 [M + H]+: 1754.2964; found [M + H]+: 1754.2938.
26a
Berndt DC.
Faburada AL.
J. Org. Chem.
1982,
47:
4167
26b
Ryng S.
Glowiak T.
Synth. Commun.
1997,
27:
1359
27
Lwowski W.
Chemistry of the Azido Groups
Interscience;
New York:
1971.
Chap. 9.
28a
Nakajima A.
Spectrochim. Acta, Part A
1974,
30:
860
28b
Nakajima A.
J. Mol. Spectrosc.
1976,
61:
467