Potassium Sodium Tartrate → HCID 69624823, compound

HRID 397286Notes

Reaction equation

HRID 397286 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:19]2([O:49][C@H:48]([CH2:50][O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C@@H:39]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@H:30]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@@H:21]2[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[OH:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH:19]([OH:20])[C@H:21]([C@H:30]([C@@H:39]([C@@H:48]([CH2:50][O:51][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[OH:49])[O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 69624821HCID 69624821, compound

Product 1

HCID 69624823HCID 69624823, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

First, 7.74 g (9.72 mmol) of 1-C-[1-(phenylsulfonyl)indole-2-yl]-2,3,4,6-tetra-O-benzyl-D-mannopyranose [compound (IV) wherein R1 to R4 are benzyl and R5 is phenylsulfonyl] was dissolved in tetrahydrofuran (240 ml). Then, 1.11 g (29.25 mmol) of lithium aluminum hydride was added to the mixture and stirred at about 0° C. for about 30 minutes. After the reaction was completed, a saturated aqueous solution of Rochelle salt was added to the reaction mixture which was then subjected to extraction with diethylether. The ether solution was washed with saturated saline and then dried on anhydrous sodium sulfate. After removal of the solvent by distillation, the residue was fractionated by column chromatography on silica gel [silica gel: Merck Kieselgel 60 (230-400 mesh ASTM); elution solvent: n-hexane and ethyl acetate (5:2)] to give 5.85 g (yield 75%) of 1-C-[1-(phenylsulfonyl)indole-2-yl]-2,3,4,6-tetra-O-benzyl-D-mannitol [compound (V) wherein R1 to R4 are benzyl and R5 is phenylsulfonyl].

Workup

  1. extractionwas then subjected to extraction with diethylether
  2. washThe ether solution was washed with saturated saline
  3. dry with materialdried on anhydrous sodium sulfate
  4. customAfter removal of the solvent
  5. distillationby distillation

Sources & evidence

ORD record
ord-a401017cd0b148708b5c72214af9ba02
Source dataset
uspto-grants-2003_08
Patent number
US06610502B1

Reaction notes

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