Peptidosulfonamides
863
H3), 7.25 (s, 5H, Ph); 13C NMR (CDCl3) d: 32.6 (C5), 45.9 (CH2N), 51.6 (C4),
62.6 (OCH2Ph), 64.1 (CH2O), 66.3, 66.4ꢁ (C1), 127.7 (Ph), 128.2 (C3), 128.4
(Ph), 129.2 (Ph), 137.4 (C2), 138.1 (Ph), 156.0 (NCOO); MS (ESI), m/z: 351
(M þ H)þ.
(Z) Isobutylsulfinamoyl-cyclopent-2-enyl-4-carbamic acid benzyl ester
1
2c: H NMR (200 MHz CDCl3) d: 0.92 (d, 6H, J ¼ 6.8 Hz, CH3CH), 1.68
(m, 1H, CH3CH), 1.81 (dt, 1H, J ¼ 14.9, 1.7 Hz, cis H5), 2.5 (dt, 1H,
J ¼ 14.9, 7.9 Hz, trans H5), 2.90 (m, 2H, CH2N), 3.94 (m, 1H, H1), 4.80
(m, 1H, H4), 5.08 (s, 2H, OCH2Ph), 6.05 (m, 2H, H2-H3), 7.28 (s, 5H, Ph);
13C NMR (CDCl3) d: 19.8 (CH3CH), 30.0 (CH3CH) 33.1 (C5), 52.1 (C4),
55.3 (CH2N), 66.6 (OCH2Ph), 68.0 (C1), 127.8 (Ph), 127.9 (Ph), 128.3 (C3),
128.4 (Ph), 133.1 (Ph), 136.2 (C2), 156.9 (NCOO); MS (ESI), m/z: 337
(M þ H)þ, 359 (M þ Na)þ, 695 (2M þ Na)þ.
(Z) Benzylsulfinamoyl-cyclopent-2-enyl-4-carbamic acid benzyl ester 2d:
1H NMR (200 MHz CDCl3) d: 1.90, (dt, 1H, J ¼ 14.1, 5.05 Hz, cis H5), 2.81
(dt, 1H, J ¼ 14.1, 7.7 Hz, trans H5), 3.24 (m, 1H, H1), 4.05 (s, 2H, NCH2Ph),
4.60 (m, 1H, H4), 4.95 (s, 2H, OCH2Ph), 5.90 (m, 2H, H2-H3), 7.2 (m, 10H,
Ph); MS (ESI), m/z: 393 (M þ Na)þ, 763 (2M þ Na)þ.
(+)-Cis-4-amino-benzyloxycarbonil-cyclopent-2-ene-1-sulfinamoyl-(S)-
valine methyl ester 2e: 1H NMR (400 MHz CD3OD) d: 0.97, 1.03ꢁ (2d, 12H,
J ¼ 2.45 Hz, CH3CH), 1.75, 2.00ꢁ (2dt, 2H, J ¼ 14.9, 4.2 Hz, cis H5), 2.25
(m, 2H, CH3CH), 2.48 (m, 2H, trans, H5), 3.64 (m, 2H, H1), 3.75 (s, 6H,
OCH3), 4.05 (m, 2H, a-CH), 4.68 (m, 2H, H4), 4.98, 5.02ꢁ (2s, 4H,
OCH2Ph), 5.94 (m, 4H, H2,3), 7.22 (s, 10H, Ph); 13C NMR (CD3OD) d:
18.1, 18.3ꢁ (CH3CH), 30.0 (CH3CH), 30.9, 31.6ꢁ (C5), 55.7, 55.8ꢁ (OCH3),
56.7, 57.1ꢁ (C4), 59.3, 59.7ꢁ (a-CH), 64.4, 65.7ꢁ (C1), 67.1, 67.4ꢁ
(OCH2Ph), 128.9, 129.3ꢁ (C3), 127.8, 127.9ꢁ, 128.1, 128.5ꢁ, 128.7, 129.3ꢁ,
138.5, 138.7ꢁ (Ph), 139, 139.6ꢁ (C4), 157.6 (NCOO), 170.3 (COOCH3). MS
(ESI), m/z: 395 (M þ H)þ.
(+)-cis-4-amino-benzyloxycarbonyl-cyclopent-2-ene-1-sulfinamoyl-(S)-
1
triptophane methyl ester 2f: H NMR (200 MHz CD3OD) d: 1.75, 2.02ꢁ
(2dt, 2H, J ¼ 14.6, 3.8 Hz, cis H5), 2.48 (m, 2H, trans H5), 3.31 (m, 4H,
CH2–Ind), 3.60 (s, 6H, OCH3), 3.71 (m, 2H, H1), 4.25 (m, 2H, a-CH), 4.72
(m, 2H, H4), 5.03, 5.05ꢁ (2s, 2H, OCH2Ph), 5.89 (m, 4H, H2,H3), 7.00–7.65
(m, 20H, Ph, Ind); MS (ESI), m/z: 482 (M þ H)þ.
(+)-Cis-4-amino-benzyloxycarbonyl-cyclopent-2-ene-1-sulfinamoyl-(S)-
proline methyl ester 2g: 1H NMR (200 MHz CDCl3) d: 1.50–1.78 (m, 10H,
NCH2CH2CH2; cis H5), 1.90–2.11 (m, 2H, trans H5), 2.60–2.95 (m, 4H,
*
Double signals due to the presence of diastereoisomers.