Potassium Hydroxide → Octapotassium (2R,3R,4S,5R,6R)-2-(((2S,3S,4R,5R)-3,4-disulfato-2,5-bis(sulfatomethyl)oxolane-2-yl)oxy)-3,4,5-trisulfato-6-(sulfatomethyl)oxane

HRID 963967Notes

Reaction equation

HRID 963967 reaction equation
[CH2:1]([O:51][S:52]([OH:55])(=[O:54])=[O:53])[C@H:2]1[O:7][C@H:6]([O:8][C@:9]2([CH2:30][O:31][S:32]([OH:35])(=[O:34])=[O:33])[O:13][C@H:12]([CH2:14][O:15][S:16]([OH:19])(=[O:18])=[O:17])[C@@H:11]([O:20][S:21]([OH:24])(=[O:23])=[O:22])[C@@H:10]2[O:25][S:26]([OH:29])(=[O:28])=[O:27])[C@H:5]([O:36][S:37]([OH:40])(=[O:39])=[O:38])[C@@H:4]([O:41][S:42]([OH:45])(=[O:44])=[O:43])[C@@H:3]1[O:46][S:47]([OH:50])(=[O:49])=[O:48].[OH-].[K+:57]>>[CH2:1]([O:51][S:52]([O-:55])(=[O:53])=[O:54])[C@H:2]1[O:7][C@H:6]([O:8][C@:9]2([CH2:30][O:31][S:32]([O-:35])(=[O:34])=[O:33])[O:13][C@H:12]([CH2:14][O:15][S:16]([O-:19])(=[O:17])=[O:18])[C@@H:11]([O:20][S:21]([O-:24])(=[O:23])=[O:22])[C@@H:10]2[O:25][S:26]([O-:29])(=[O:28])=[O:27])[C@H:5]([O:36][S:37]([O-:40])(=[O:38])=[O:39])[C@@H:4]([O:41][S:42]([O-:45])(=[O:44])=[O:43])[C@@H:3]1[O:46][S:47]([O-:50])(=[O:49])=[O:48].[K+:57].[K+:57].[K+:57].[K+:57].[K+:57].[K+:57].[K+:57].[K+:57]

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 444237Sucrosofate

Product 1

HCID 71947Octapotassium (2R,3R,4S,5R,6R)-2-(((2S,3S,4R,5R)-3,4-disulfato-2,5-bis(sulfatomethyl)oxolane-2-yl)oxy)-3,4,5-trisulfato-6-(sulfatomethyl)oxane

Procedure

One portion of sucrose octasulfate solution prepared as described in I above was adjusted with 10% w/w aqueous potassium hydroxide to pH=9 with stirring at room temperature. The solution was evaporated at 50° C. in vacuo to remove pyridine and water until 880 g were left. The warm solution was filtered, adjusted to pH=9.5, and the substance was precipitated with slow cooling to 5° C. The substance was filtered and washed with 300 ml of 1:1 ion-exchanged water/methanol and 300 ml of methanol. The wet filter cake was dried in vacuo at 50° C. The crude product was dissolved at 40° C. in 700 ml of ion-exchanged water. The liquid was filtered and adjusted to pH=9.5, and the substance was precipitated with slow cooling to 5° C. The precipitated substance was filtered and washed with 300 ml of 1:1 ion-exchanged water/methanol and 300 ml of methanol. The wet filter cake was dried in vacuo at 50° C. The substance was reprecipitated twice as mentioned above.

Workup

  1. customThe solution was evaporated at 50° C. in vacuo
  2. customto remove pyridine and water until 880 g
  3. waitwere left
  4. filtrationThe warm solution was filtered
  5. customthe substance was precipitated
  6. temperaturewith slow cooling to 5° C
  7. filtrationThe substance was filtered
  8. washwashed with 300 ml of 1:1 ion-exchanged water/methanol and 300 ml of methanol
  9. customThe wet filter cake was dried in vacuo at 50° C
  10. dissolutionThe crude product was dissolved at 40° C. in 700 ml of ion-exchanged water
  11. filtrationThe liquid was filtered
  12. customthe substance was precipitated
  13. temperaturewith slow cooling to 5° C
  14. filtrationThe precipitated substance was filtered
  15. washwashed with 300 ml of 1:1 ion-exchanged water/methanol and 300 ml of methanol
  16. customThe wet filter cake was dried in vacuo at 50° C
  17. customThe substance was reprecipitated twice

Sources & evidence

ORD record
ord-0ca9191d081d4cdfaf602c7117a367ac
Source dataset
uspto-grants-1998_06
Patent number
US05767104

Reaction notes

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