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

HRID 851675Notes

Reaction equation

HRID 851675 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:103]([NH:105][C@H:106]([C:140]([OH:142])=[O:141])[CH2:107][CH2:108][CH2:109][CH2:110][NH:111][C:112](=[O:139])[CH2:113][CH2:114][S:115][C@H:116]1[O:133][C@H:132]([CH2:134][O:135]C(=O)C)[C@@H:127]([O:128]C(=O)C)[C@H:122]([O:123]C(=O)C)[C@@H:117]1[O:118]C(=O)C)=[O:104])[CH2:70][CH2:71][CH2:72][CH2:73][NH:74][C:75](=[O:102])[CH2:76][CH2:77][S:78][C@H:79]1[O:96][C@H:95]([CH2:97][O:98]C(=O)C)[C@@H:90]([O:91]C(=O)C)[C@H:85]([O:86]C(=O)C)[C@@H:80]1[O:81]C(=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:103]([NH:105][C@H:106]([C:140]([OH:142])=[O:141])[CH2:107][CH2:108][CH2:109][CH2:110][NH:111][C:112](=[O:139])[CH2:113][CH2:114][S:115][C@H:116]2[O:133][C@H:132]([CH2:134][OH:135])[C@@H:127]([OH:128])[C@H:122]([OH:123])[C@@H:117]2[OH:118])=[O:104])[CH2:70][CH2:71][CH2:72][CH2:73][NH:74][C:75](=[O:102])[CH2:76][CH2:77][S:78][C@H:79]2[O:96][C@H:95]([CH2:97][OH:98])[C@@H:90]([OH:91])[C@H:85]([OH:86])[C@@H:80]2[OH:81])=[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 86738900N2 {N2-{N2,N6-Bis[3-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosylthio)propionyl]-L-lysyl}-N6-[3-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosylthio)propionyl]-L-lysyl}-N6-[3-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosylthio)propionyl]-L-lysine

Product 1

HCID 86738899N2 {N2-{N2,N6-Bis[3-(alpha-D-mannopyranosylthio)propionyl]-L-lysyl}-N6-[3-(alpha-D-mannopyranosylthio)propionyl]-L-lysyl}-N6-[3-(alpha-D-mannopyranosylthio)propionyl]-L-lysineYield 71%

Reagents, catalysts & solvents 1

HCID 23434731Methanol water triethylamineSolvent

Procedure

A solution of 15 (52 mg, 0.025 mmol) in methanol-water-triethylamine 5:4:1 (v/v/v, 1 ml) is kept for 3 hours at room temperature, and evaporated in vacuo to a residue that is put on a Sephadex G-15 column and eluted with water. Fractions 1-4 (12 ml), eluted after blue dextran, are collected and lyophilized to give 16 (25.1 mg, 71%): [α]D27 +96.2° (c 1.0, H2O); NMR (D2O)δ: 5.37 (s, 1H, H-1), 5.34 (s, 3H, H-1) 4.34 (2H), 4.18 (1H) (α-CH), 3.22 (m, ε-CH2), 2.93 (m, SCH2), 2.70 (t, 2H), 2.60 (t, 6H) (SCH2CH2), 1.34-1.94 (CCH2CH2CH2C).

Workup

  1. customevaporated in vacuo to a residue that
  2. washeluted with water
  3. washFractions 1-4 (12 ml), eluted after blue dextran
  4. customare collected

Sources & evidence

ORD record
ord-94861e4f1f3646ac8b74bb95b4669779
Source dataset
uspto-grants-1983_05
Patent number
US04386026

Reaction notes

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