Tetrahydrofuran → HCID 11657654, compound

HRID 1869608Notes

Reaction equation

HRID 1869608 reaction equation
[Na].C([O:5][C@@H:6]1[C@@H:11]([NH:12][C:13](=[O:24])[C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[CH:15]=2)[C@@H:10]([O:25]C(=O)C)[C@@H:9]([CH2:29][O:30]C(=O)C)[O:8][C@H:7]1[S:34][C@@H:35]1[O:48][C@H:47]([CH2:49][O:50]C(=O)C)[C@H:42]([O:43]C(=O)C)[C@H:41]([NH:54][C:55](=[O:66])[C:56]2[CH:61]=[C:60]([O:62][CH3:63])[CH:59]=[C:58]([O:64][CH3:65])[CH:57]=2)[C@H:36]1[O:37]C(=O)C)(=O)C.C[O-].[Na+].C1COCC1>CO>[CH3:63][O:62][C:60]1[CH:61]=[C:56]([CH:57]=[C:58]([O:64][CH3:65])[CH:59]=1)[C:55]([NH:54][C@H:41]1[C@@H:42]([OH:43])[C@@H:47]([CH2:49][OH:50])[O:48][C@@H:35]([S:34][C@@H:7]2[O:8][C@H:9]([CH2:29][OH:30])[C@H:10]([OH:25])[C@H:11]([NH:12][C:13](=[O:24])[C:14]3[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[CH:15]=3)[C@H:6]2[OH:5])[C@@H:36]1[OH:37])=[O:66]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 86613987HCID 86613987, compound

Product 1

HCID 11657654HCID 11657654, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium (1.5 mg, 0.07 mmol) was dissolved in methanol (1 ml). Bis(2,4,6-tri-O-acetyl-3-deoxy-3-(3,5-dimethoxybenzamido)-β-D-galactopyranosyl) sulfane 14 (11 mg, 0.012 mmol) was dissolved in methanol (1 ml) and the sodium methoxide solution was added. The mixture was stirred at room temperature for 3 h. After this time, a precipitate had appeared. THF (3 ml) was added, and the precipitate dissolved. Duolite C436 (H+) was added, and the mixture was stirred for 5 minutes. After this time, the mixture was filtered and concentrated in vacuo. The residue was purified by HPLC (gradient H2O→MeCN) to give bis(3-deoxy-3-(3,5-dimethoxybenzamido)-β-D-galactopyranosyl) sulfane 19 (4.7 mg, 58%). White solid;

Workup

  1. dissolutionthe precipitate dissolved
  2. additionDuolite C436 (H+) was added
  3. stirringthe mixture was stirred for 5 minutes
  4. filtrationAfter this time, the mixture was filtered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by HPLC (gradient H2O→MeCN)

Sources & evidence

ORD record
ord-a3940a00dcf74b31ab3036468a6a0bc8
Source dataset
uspto-grants-2009_12
Patent number
US07638623B2

Reaction notes

Loading…