Sodium Hydroxide → HCID 9889037, compound

HRID 2400141Notes

Reaction equation

HRID 2400141 reaction equation
OCC1SSC(CO)=CC=1.C[C@:12]1([O:25][CH2:26][C:27]2[S:28][S:29][C:30]([CH2:33][O:34][C@@:35]3(C)[O:44][C@H:43]([C:45]([O-])=[O:46])[C@@H:38]([O:39]C(=O)C)[CH:37]=[CH:36]3)=[CH:31][CH:32]=2)[O:21][C@H:20]([C:22]([O-])=[O:23])[C@@H:15]([O:16]C(=O)C)[CH:14]=[CH:13]1.[OH-].[Na+]>C1COCC1>[C@H:12]1([O:25][CH2:26][C:27]2[S:28][S:29][C:30]([CH2:33][O:34][C@H:35]3[O:44][C@H:43]([CH2:45][OH:46])[C@@H:38]([OH:39])[CH:37]=[CH:36]3)=[CH:31][CH:32]=2)[O:21][C@H:20]([CH2:22][OH:23])[C@@H:15]([OH:16])[CH:14]=[CH:13]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 462608155698-98-9HCID 86749008HCID 86749008, compound

Product 1

HCID 9889037HCID 9889037, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By the above procedure for glycosylation of 3,6-bis(hydroxymethyl)-1,2-dithiin but using methyl 3,4-diacetyl-1,2-dideoxy-D-arabinohexenopyranosyluronate instead of triacetyl D-glucal, the product obtained after work-up is 3,6-di[methyl 4-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyluronate]oxymethyl-1,2-dithiin (17B). This diacetate dimethyl ester (20 mg) dissolved in 1 mL of THF is treated with 3 mL of 0.1M aqueous NaOH, and the resulting solution is stirred at room temperature for three hours. The hydrolyzed product is extracted, the extract layers are combined and dried, and the solvent removed. After purification by silica gel chromatography, the product is 3,6-di[sodium 2,3-dideoxy-α-D-erythro-hex-2-enopyranosyluronate]oxymethyl-1,2-dithiin (8B).

Workup

  1. customthe product obtained after work-up
  2. extractionThe hydrolyzed product is extracted
  3. customdried
  4. customthe solvent removed
  5. customAfter purification by silica gel chromatography

Sources & evidence

ORD record
ord-76842048698543408d611f875bcd8aac
Source dataset
uspto-grants-1995_09
Patent number
US05453500

Reaction notes

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