HCID 13384941, compound → HCID 54192326, compound

HRID 2417858Notes

Reaction equation

HRID 2417858 reaction equation
C([O:4][C@@H:5]1[C@@H:18]([O:19]C(=O)C)[C@H:17]([O:23][C@H:24]2[O:41][C@H:40]([CH2:42][O:43]C(=O)C)[C@@H:35]([O:36]C(=O)C)[C@H:30]([O:31]C(=O)C)[C@H:25]2[O:26]C(=O)C)[C@@H:16]([CH2:47][O:48]C(=O)C)[O:15][C@H:6]1[S:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)(=O)C>C(N(CC)CC)C.CO.O>[C@H:24]1([O:23][C@@H:17]2[C@@H:16]([CH2:47][OH:48])[O:15][C@@H:6]([S:7][C:8]3[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=3)[C@H:5]([OH:4])[C@H:18]2[OH:19])[O:41][C@H:40]([CH2:42][OH:43])[C@@H:35]([OH:36])[C@H:30]([OH:31])[C@H:25]1[OH:26]

Participants

3

Reactant 1

HCID 13384941HCID 13384941, compound

Product 1

HCID 54192326HCID 54192326, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 23434731Methanol water triethylamineSolvent

Procedure

A solution of 4.0 g of 4-hydroxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside in 53 ml of a mixture of 2N triethylamine:methanol:water (3:6:2) was stirred for 4 hours, chilled overnight and then concentrated to an oil. This oil was dissolved in water, extracted with three 500 ml portions of ether and both the water and ether layers were concentrated and combined. The combined concentrate was dissolved in 200 ml of water, acidified to pH 4 and chromatographed on Amberlite® XAD-2 resin, eluting with 500 ml of water, then 500 ml of methanol. The methanol extract was concentrated, giving 1.2 g of the desired intermediate [α]D26 =+31°±1° (1.144%, methanol).

Workup

  1. temperaturechilled overnight
  2. concentrationconcentrated to an oil
  3. dissolutionThis oil was dissolved in water
  4. extractionextracted with three 500 ml portions of ether and both the water and ether layers
  5. concentrationwere concentrated
  6. concentrationThe combined concentrate
  7. dissolutionwas dissolved in 200 ml of water
  8. customchromatographed on Amberlite® XAD-2 resin
  9. washeluting with 500 ml of water
  10. extractionThe methanol extract
  11. concentrationwas concentrated

Sources & evidence

ORD record
ord-56a45bdea89b4659b1c04b0f3edb0357
Source dataset
uspto-grants-1984_09
Patent number
US04470976

Reaction notes

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