References and Notes
1
Soth MJ.
Nowick JS.
Curr. Opin. Chem. Biol.
1997,
1:
120
2
Schneider SE.
Anslyn EV.
Molecular Recognition and Solid Phase Organic Synthesis: Synthesis of Unnatural Oligomers, Techniques for Monitoring Reactions, and the Analysis of Combinatorial Libraries, In Advances in Supramolecular Chemistry
Vol. 5:
Gokel GW.
JAI Press;
Stamford CT:
1999.
p.55-120
3
Kirshenbaum K.
Zuckermann RN.
Dill KA.
Curr. Opin. Struct. Biol.
1999,
9:
530
4
Cheng RP.
Gellman SH.
DeGrado WF.
Chem. Rev.
2001,
101:
3219
5
Hill DJ.
Mio MJ.
Prince RB.
Hughes TS.
Moore JS.
Chem. Rev.
2001,
101:
3893
6
Oh K.
Jeong KS.
Moore JS.
Nature (London)
2001,
414:
889
7
Burgess K.
Linthicum DS.
Shin HW.
Angew. Chem., Int. Ed. Engl.
1995,
34:
907
8
Kim JM.
Bi YZ.
Paikoff SJ.
Schultz PG.
Tetrahedron Lett.
1996,
37:
5305
9
Burgess K.
Ibarzo J.
Linthicum DS.
Russell DH.
Shin H.
Shitangkoon A.
Totani R.
Zhang AJ.
J. Am. Chem. Soc.
1997,
119:
1556
10
Boeijen A.
van Ameijde J.
Liskamp RMJ.
J. Org. Chem.
2001,
66:
8454
11
Guichard G.
Semetey V.
Rodriguez M.
Briand J.-P.
Tetrahedron Lett.
2000,
41:
1553
12
Dempcy RO.
Luo J.
Bruice TC.
Proc. Natl. Acad. Sci. U.S.A.
1996,
93:
4326
13
Tanatani A.
Kagechika H.
Azumaya I.
Fukutomi R.
Ito Y.
Yamaguchi K.
Shudo K.
Tetrahedron Lett.
1997,
38:
4425
14
Schneider SE.
Bishop PA.
Salazar MA.
Bishop OA.
Anslyn EV.
Tetrahedron
1998,
54:
15063
15
Tanatani A.
Yamaguchi K.
Azumaya I.
Fukutomi R.
Shudo K.
Kagechika H.
J. Am. Chem. Soc.
1998,
120:
6433
16
Linkletter BA.
Bruice TC.
Bioorg. Med. Chem. Lett.
1998,
8:
1285
17
Linkletter BA.
Szabo IE.
Bruice TC.
J. Am. Chem. Soc.
1999,
121:
3888
18
Linkletter BA.
Bruice TC.
Bioorg. Med. Chem.
2000,
8:
1893
19
Zhang Z.
Carter T.
Fan E.
Tetrahedron Lett.
2003,
44:
3063
20
Zhang Z.
Fan E.
J. Org. Chem.
2005,
70:
8801
21
Horwell DC.
Hughes J.
Hunter JC.
Pritchard MC.
Richardson RS.
Roberts E.
Woodruff GN.
J. Med. Chem.
1991,
34:
404
22
Tornoe CW.
Christensen C.
Meldal M.
J. Org. Chem.
2002,
67:
3057
23
Wolff H.
Schmidt Reaction, In Organic Reactions
Vol. 3:
Adams R.
Bacjmann WE.
Fieser LF.
Johnson JR.
Snyder HR.
John Wiley and Sons;
New York:
1947.
p.307-336
24
Garegg PJ.
Samuelsson B.
J. Chem. Soc., Chem. Commun.
1979,
978
25
Benito JM.
Christensen CA.
Meldal M.
Org. Lett.
2005,
7:
581
26
Olsen CA.
Witt M.
Jaroszewski JW.
Franzyk H.
Org. Lett.
2004,
6:
1935
27
Rodriguez M.
Llinares M.
Doulut S.
Heitz A.
Martinez J.
Tetrahedron Lett.
1991,
32:
923
28 All compounds gave satisfactory analytical data. Described below are a representative procedure and spectral data for Fmoc-protected glutamate azide 2h. Fmoc-protected glutamate alcohol 1h (50 mg, 0.12 mmol) in dry CH2Cl2 was added to a pre-mixed (5 min) solution of PPh3 (94 mg, 0.36 mmol, 3 equiv), iodine (91 mg, 0.36 mmol, 3 equiv) and imidazole (41 mg, 0.6 mmol, 5 equiv) in 1.2 mL dry CH2Cl2. The reaction mixture was stirred at r.t. for 1.5 h. After completion of the reaction the solvent was evaporated at reduced pressure and the corresponding iodide was purified by silica gel column chromatography (10% EtOAc in hexane). The iodide was then dissolved in 0.5 mL DMF, mixed with NaN3 (39 mg, 0.6 mmol, 5 equiv with respect to alcohol 1h) and stirred at r.t. for 3.5 h. After solvent removal and silica gel column chromatography (10% EtOAc in hexane), azide 2h was obtained as a white solid in high yield. Yield 50 mg (94% overall from alcohol 1h); mp 65-66 °C. 1H NMR (CDCl3): δ = 1.47 (s, 9 H), 1.82-1.86 (m, 2 H), 2.29-2.36 (m, 2 H), 3.42-3.48 (m, 2 H), 3.75-3.87 (br m, 1 H), 4.23 (t, 1 H, J = 6.9 Hz), 4.38-4.50 (m, 2 H), 5.03 (d, 1 H, J = 7.7 Hz), 7.31-7.45 (m, 4 H), 7.61 (d, 2 H, J = 7.2 Hz), 7.79 (d, 2 H, J = 7.2 Hz). ESI-MS: m/z = 437.0 [M + H]+.
Additional list of 1H NMR of new compounds:
Compound 2g: 1H NMR (CDCl3): δ = 1.76-1.83 (m, 2 H), 2.29-2.31 (m, 2 H), 3.31-3.37 (m, 2 H), 3.72 (br m, 1 H), 4.20 (t, 1 H, J = 6.5 Hz), 4.37-4.50 (m, 2 H), 5.01 (d, 1 H, J = 7.9 Hz), 6.75 (s, 1 H), 7.18-7.29 (m, 17 H), 7.35-7.41 (m, 2 H), 7.57 (d, 2 H, J = 7.4 Hz), 7.74 (d, 2 H, J = 7.4 Hz).
Compound 2i: 1H NMR (CDCl3): δ = 1.42 (s, 6 H), 1.41-1.58 (m, 4 H), 2.06 (s, 3 H), 2.49 (s, 3 H), 2.56 (s, 3 H), 2.90 (s, 2 H), 3.16-3.31 (m, 4 H), 3.72 (br m, 1 H), 4.14 (t, 1 H, J = 6.5 Hz), 4.32-4.41 (m, 2 H), 5.30 (d, 1 H, J = 8.4 Hz), 6.34 (br s, 2 H), 7.24-7.27 (m, 2 H), 7.34-7.38 (m, 2 H), 7.54-7.55 (m, 2 H), 7.73 (d, 2 H, J = 7.4 Hz).
Compound 2j: 1H NMR (CDCl3): δ = 1.65 (s, 9 H), 2.93-2.99 (m, 2 H), 3.45-3.49 (m, 2 H), 4.17-4.22 (m, 2 H), 4.41-4.43 (m, 2 H) 4.98 (d, 1 H, J = 7.8 Hz), 7.27-7.41 (m, 6 H), 7.46-7.63 (m, 4 Hz), 7.76 (d, 2 H, J = 7.4 Hz), 8.14 (br s, 1 H).