Water → (2S,3R,4R,5S,6R)-2-[3-(Benzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]-6-hydroxymethyltetrahydro-pyran-3,4,5-triol

HRID 550231Notes

Reaction equation

HRID 550231 reaction equation
CSC.[S:4]1[C:8]([CH2:9][C:10]2[CH:11]=[C:12]([C@H:20]3[C@@H:25]([O:26]CC4C=CC=CC=4)[C@@H:24]([O:34]CC4C=CC=CC=4)[C@@H:23]([O:42]CC4C=CC=CC=4)[C@@H:22]([CH2:50][O:51]CC4C=CC=CC=4)[O:21]3)[C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][C:6]2[CH:59]=[CH:60][CH:61]=[CH:62][C:5]1=2.O>C(Cl)Cl>[S:4]1[C:8]([CH2:9][C:10]2[CH:11]=[C:12]([C@H:20]3[C@H:25]([OH:26])[C@@H:24]([OH:34])[C@H:23]([OH:42])[C@@H:22]([CH2:50][OH:51])[O:21]3)[C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][C:6]2[CH:59]=[CH:60][CH:61]=[CH:62][C:5]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 1068Dimethyl SulfideHCID 67157507(2S,3R,4R,5S,6R)-2-[3-(Benzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran

Product 1

HCID 11633504(2S,3R,4R,5S,6R)-2-[3-(Benzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]-6-hydroxymethyltetrahydro-pyran-3,4,5-triolYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, dimethylsulfide (3.5 ml) and boron trifluoride-diethyl ether complex (1.75 ml, 13.8 mmol) were added dropwise to an solution of (2S,3R,4R,5S,6R)-2-[3-(benzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran (1.1 g, 1.38 mmol) in anhydrous methylene chloride (30 ml) at 0° C. and the reaction mixture was stirred at room temperature for three days. Water (10 ml) was added thereto and the resulting mixture was then extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate. After filtration, the solvent was distilled under reduced pressure, and the obtained residue was purified by silica gel flash column chromatography [methylene chloride:methanol (30:1)] to obtain the title compound (0.35 g, 58.2%).

Workup

  1. extractionthe resulting mixture was then extracted with methylene chloride
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. distillationthe solvent was distilled under reduced pressure
  6. customthe obtained residue was purified by silica gel flash column chromatography [methylene chloride:methanol (30:1)]

Sources & evidence

ORD record
ord-16c2c604a8344cdc839cb789c171c9a4
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

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