HCID 69624823, compound → HCID 69624850, compound

HRID 397287Notes

Reaction equation

HRID 397287 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[CH:19](O)[C@H:20]([C@H:29]([C@@H:38]([C@@H:47]([CH2:49][O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[OH:48])[O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1(C)C=CC=CC=1>[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@H:19]2[O:48][C@H:47]([CH2:49][O:50][CH2:51][C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[C@@H:38]([O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C@H:29]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:20]2[O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 69624823HCID 69624823, compound

Product 1

HCID 69624850HCID 69624850, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

First, 5.85 g (7.33 mmol) 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]was dissolved in toluene (500 ml). Then, 0.70 g (3.68 mmol) of paratoluene sulfate monohydrate was added to the mixture and stirred at about 100° C. for about 1 hour. After the reaction was terminated, a saturated solution of sodium hydrogen carbonate in water was added to the reaction mixture which was then subjected to extraction with diethylether. The ether solution was washed with saturated saline and 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: dichloromethane] to give 3.31 g (yield 58%) of (1R)-1,5-anhydro-1-C-[1-(phenylsulfonyl)indole-2-yl]-2,3,4,6-tetra-O-benzyl-D-mannitol [compound (VI) wherein R1 to R4 are benzyl and R5 is phenylsulfonyl].

Workup

  1. customAfter the reaction was terminated
  2. additiona saturated solution of sodium hydrogen carbonate in water was added to the reaction mixture which
  3. extractionwas then subjected to extraction with diethylether
  4. washThe ether solution was washed with saturated saline
  5. dry with materialdried on anhydrous sodium sulfate
  6. customAfter removal of the solvent
  7. distillationby distillation

Sources & evidence

ORD record
ord-4e0f67bf8a4c4f34a59e738692188bc7
Source dataset
uspto-grants-2003_08
Patent number
US06610502B1

Reaction notes

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