N2 {N2,N6-Bis[3-(2,3,4--tri-O-acetyl-beta-L-fucopyranosylthio)propionyl]-L-lysyl}-N6 [3-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylthio)propionyl]-L-lysine → N2 {N2,N6-Bis[3-(beta-L-fucopyranosylthio)propionyl]-L-lysyl}-N6 [3-(beta-L-fucopyranosylthio)propionyl]-L-lysine

HRID 851678Notes

Reaction equation

HRID 851678 reaction equation
[N:1]#[N:2].C([O:6][C@H:7]1[C@H:12]([O:13]C(=O)C)[C@H:11]([O:17]C(=O)C)[C@H:10]([CH3:21])[O:9][C@@H:8]1[S:22][CH2:23][CH2:24][C:25]([NH:27][C@H:28]([C:58]([NH:60][C@H:61]([C:91]([OH:93])=[O:92])[CH2:62][CH2:63][CH2:64][CH2:65][NH:66][C:67](=[O:90])[CH2:68][CH2:69][S:70][C@H:71]1[O:88][C@@H:87]([CH3:89])[C@@H:82]([O:83]C(=O)C)[C@@H:77]([O:78]C(=O)C)[C@@H:72]1[O:73]C(=O)C)=[O:59])[CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:57])[CH2:35][CH2:36][S:37][C@H:38]1[O:55][C@@H:54]([CH3:56])[C@@H:49]([O:50]C(=O)C)[C@@H:44]([O:45]C(=O)C)[C@@H:39]1[O:40]C(=O)C)=[O:26])(=O)C>CO.O.C(N(CC)CC)C>[N:1]#[N:2].[C@H:8]1([S:22][CH2:23][CH2:24][C:25]([NH:27][C@H:28]([C:58]([NH:60][C@H:61]([C:91]([OH:93])=[O:92])[CH2:62][CH2:63][CH2:64][CH2:65][NH:66][C:67](=[O:90])[CH2:68][CH2:69][S:70][C@H:71]2[O:88][C@@H:87]([CH3:89])[C@@H:82]([OH:83])[C@@H:77]([OH:78])[C@@H:72]2[OH:73])=[O:59])[CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:57])[CH2:35][CH2:36][S:37][C@H:38]2[O:55][C@@H:54]([CH3:56])[C@@H:49]([OH:50])[C@@H:44]([OH:45])[C@@H:39]2[OH:40])=[O:26])[O:9][C@@H:10]([CH3:21])[C@@H:11]([OH:17])[C@@H:12]([OH:13])[C@@H:7]1[OH:6]

Participants

3

Reactant 1

HCID 86738905N2 {N2,N6-Bis[3-(2,3,4--tri-O-acetyl-beta-L-fucopyranosylthio)propionyl]-L-lysyl}-N6 [3-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylthio)propionyl]-L-lysine

Product 1

HCID 86738904N2 {N2,N6-Bis[3-(beta-L-fucopyranosylthio)propionyl]-L-lysyl}-N6 [3-(beta-L-fucopyranosylthio)propionyl]-L-lysineYield 83%

Reagents, catalysts & solvents 1

HCID 23434731Methanol water triethylamineSolvent

Procedure

A solution of 25 (500 mg) in methanol-water-triethylamine 5:4:1 (v/v/v, 5 ml) is kept for 3 hours at room temperature and worked-up in the same manner as for 5 to give the title compound (300 mg, 83%): [α]D27 +28.4±0.9° (c 1.0 H2O); NMR (D2O)δ: 4.48 (d, J1,2 =9.5 Hz, 1H, H-1), 4.46 (d, J1,2 =9.5 Hz, 2H, H-1), 4.17, 4.32 (q,q, α-CH), 3.22 (m, ε-CH2), 2.98 (m, SCH2), 2.69 (t, 1H), 2.61 (t, 2H) (SCH2CH2), 1.34-1.90 (m, C-CH2CH2CH2C), 1.25 (d, J=6.0 Hz, CH3 -6).

Sources & evidence

ORD record
ord-70a7f9c0585a4a52bf6acaa3dd541fdd
Source dataset
uspto-grants-1983_05
Patent number
US04386026

Reaction notes

Loading…