HCID 13384939, compound → HCID 53814890, compound

HRID 2417857Notes

Reaction equation

HRID 2417857 reaction equation
C([O:4][C@@H:5]1[C@@H:20]([O:21]C(=O)C)[C@H:19]([O:25][C@H:26]2[O:43][C@H:42]([CH2:44][O:45]C(=O)C)[C@@H:37]([O:38]C(=O)C)[C@H:32]([O:33]C(=O)C)[C@H:27]2[O:28]C(=O)C)[C@@H:18]([CH2:49][O:50]C(=O)C)[O:17][C@H:6]1[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([OH:16])=[O:15])(=O)C>C(N(CC)CC)C.CO.O>[C@H:26]1([O:25][C@@H:19]2[C@@H:18]([CH2:49][OH:50])[O:17][C@@H:6]([S:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:14]([OH:16])=[O:15])[C@H:5]([OH:4])[C@H:20]2[OH:21])[O:43][C@H:42]([CH2:44][OH:45])[C@@H:37]([OH:38])[C@H:32]([OH:33])[C@H:27]1[OH:28]

Participants

3

Reactant 1

HCID 13384939HCID 13384939, compound

Product 1

HCID 53814890HCID 53814890, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 23434731Methanol water triethylamineSolvent

Procedure

A solution of 1.6 g of 2-carboxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside in 15 ml of a mixture of 2N triethylamine:methanol:water (3:6:2) was stirred for 16 hours, then concentrated in vacuo to a solid. This solid was dissolved in water, adjusted to pH 3.5, diluted further with water producing a slurry which was applied to 150 ml of a polystyrene resin, for example, Amberlite® XAD-2 resin (Norman Haase) and then eluted with 500 ml of water followed by one liter of 80% methanol. The methanol eluate give 0.6 g of the desired intermediate as a solid.

Workup

  1. concentrationconcentrated in vacuo to a solid
  2. dissolutionThis solid was dissolved in water
  3. additiondiluted further with water producing a slurry which
  4. washeluted with 500 ml of water

Sources & evidence

ORD record
ord-7a8ba41c57a94cf184b27793857b4136
Source dataset
uspto-grants-1984_09
Patent number
US04470976

Reaction notes

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