Sodium → HCID 54031043, compound

HRID 2417855Notes

Reaction equation

HRID 2417855 reaction equation
C([O:4][C@@H:5]1[C@@H:19]([O:20]C(=O)C)[C@H:18]([O:24][C@H:25]2[O:42][C@H:41]([CH2:43][O:44]C(=O)C)[C@@H:36]([O:37]C(=O)C)[C@H:31]([O:32]C(=O)C)[C@H:26]2[O:27]C(=O)C)[C@@H:17]([CH2:48][O:49]C(=O)C)[O:16][C@H:6]1[S:7][C:8]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=1[OH:15])(=O)C.[Na]>CO>[C@H:25]1([O:24][C@@H:18]2[C@@H:17]([CH2:48][OH:49])[O:16][C@@H:6]([S:7][C:8]3[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=3[OH:15])[C@H:5]([OH:4])[C@H:19]2[OH:20])[O:42][C@H:41]([CH2:43][OH:44])[C@@H:36]([OH:37])[C@H:31]([OH:32])[C@H:26]1[OH:27]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 13384929HCID 13384929, compound

Product 1

HCID 54031043HCID 54031043, compoundYield 107.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 14.0 g of 2,5-dihydroxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside in 100 ml of absolute methanol under argon at 5° C. was added 0.6 g of sodium spheres in oil. The reaction was stirred at room temperature for one hour, then 20 ml of a strongly acidic sulfonic acid cation exchanger, for example, Dowex® 50WX8 (H+) resin (Dow), was added, the mixture was stirred 10 minutes then filtered and concentrated in vacuo, giving 9.19 g of the desired intermediate as a dark brown solid, [α]D26 =+52°±2° (0.51% methanol).

Workup

  1. stirringthe mixture was stirred 10 minutes
  2. filtrationthen filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cbc5f9eea5e548a9a8d8db7f4867c2e0
Source dataset
uspto-grants-1984_09
Patent number
US04470976

Reaction notes

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