N2 {N2,N6-Bis[3-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosylthio)propionyl]-L-lysyl}-N6-[3-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)propionyl]-L-lysine → N2 {N2,N6-Bis[3-(beta-D-galactopyranosylthio)propionyl]-L-lysyl}-N6-[3-(beta-D-galactopyranosylthio)propionyl]-L-lysine

HRID 851676Notes

Reaction equation

HRID 851676 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]([CH2:21][O:22]C(=O)C)[O:9][C@H:8]1[S:26][CH2:27][CH2:28][C:29]([NH:31][C@H:32]([C:66]([NH:68][C@H:69]([C:102]([OH:104])=[O:103])[CH2:70][CH2:71][CH2:72][CH2:73][NH:74][C:75](=[O:101])[CH2:76][CH2:77][C@@H]1O[C@H](COC(=O)C)[C@H](OC(=O)C)[C@H](OC(=O)C)[C@H]1OC(=O)C)=[O:67])[CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:65])[CH2:39][CH2:40][S:41][C@@H:42]1[O:59][C@H:58]([CH2:60][O:61]C(=O)C)[C@H:53]([O:54]C(=O)C)[C@H:48]([O:49]C(=O)C)[C@H:43]1[O:44]C(=O)C)=[O:30])(=O)C>CO.O.C(N(CC)CC)C>[N:1]#[N:2].[C@@H:8]1([S:26][CH2:27][CH2:28][C:29]([NH:31][C@H:32]([C:66]([NH:68][C@H:69]([C:102]([OH:104])=[O:103])[CH2:70][CH2:71][CH2:72][CH2:73][NH:74][C:75](=[O:101])[CH2:76][CH2:77][S:26][C@@H:8]2[O:9][C@H:10]([CH2:21][OH:22])[C@H:11]([OH:17])[C@H:12]([OH:13])[C@H:7]2[OH:6])=[O:67])[CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:65])[CH2:39][CH2:40][S:41][C@@H:42]2[O:59][C@H:58]([CH2:60][OH:61])[C@H:53]([OH:54])[C@H:48]([OH:49])[C@H:43]2[OH:44])=[O:30])[O:9][C@H:10]([CH2:21][OH:22])[C@H:11]([OH:17])[C@H:12]([OH:13])[C@H:7]1[OH:6]

Participants

3

Reactant 1

HCID 86738903N2 {N2,N6-Bis[3-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosylthio)propionyl]-L-lysyl}-N6-[3-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)propionyl]-L-lysine

Product 1

HCID 86738902N2 {N2,N6-Bis[3-(beta-D-galactopyranosylthio)propionyl]-L-lysyl}-N6-[3-(beta-D-galactopyranosylthio)propionyl]-L-lysineYield 61%

Reagents, catalysts & solvents 1

HCID 23434731Methanol water triethylamineSolvent

Procedure

A solution of 19 (50 mg) in methanol-water-triethylamine 5:4:1 (v/v/v, 2 ml) was kept for 18 hours at room temperature, and evaporated in vacuo to dryness. The residue was put on a column of silica gel and eluted with chloroform-methanol-water 60:40:10 (v/v/v). The title compound was isolated in 61% yield (20 mg): RF 0.15 (CHCl3 -MeOH-H2O, 60:40:10); NMR (D2O)δ: 4.51 (d, J1,2 =9.5 Hz, 2H, H-1), 4.52 (d, J1,2 =9.5 Hz, 1H, H-1), 4.34, 4.18 (q, q, α-CH), 3.99 (d, J4,3 =3.0 Hz, 3H, H-4), 3.22 (m, εCH2), 3.02 (m, SCH2), 2.70 (t, J=6.5 Hz, 2H, SCH2CH2), 2.62 (t, J=6.5 Hz, 4H, SCH2CH2); [α]D27 -17.3° (c 1.5, H2O).

Workup

  1. customevaporated in vacuo to dryness
  2. washeluted with chloroform-methanol-water 60:40:10 (v/v/v)

Sources & evidence

ORD record
ord-8706c3fbb5c44bc1ac45f5d31b403956
Source dataset
uspto-grants-1983_05
Patent number
US04386026

Reaction notes

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