[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[(4-bromophenyl)methyl]-4-methyl-indolin-1-yl]tetrahydropyran-2-yl]methyl acetate → 3-(4-bromophenylmethyl)-4-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indole

HRID 2284526Notes

Reaction equation

HRID 2284526 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[CH:26]([CH2:34][C:35]3[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][CH:36]=3)[CH2:25]2)[O:7]1)(=[O:3])[CH3:2]>ClCCl.[O-2].[Mn+4].[O-2]>[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8]([N:24]2[C:32]3[C:27](=[C:28]([CH3:33])[CH:29]=[CH:30][CH:31]=3)[C:26]([CH2:34][C:35]3[CH:36]=[CH:37][C:38]([Br:41])=[CH:39][CH:40]=3)=[CH:25]2)[O:7]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 118021460[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[(4-bromophenyl)methyl]-4-methyl-indolin-1-yl]tetrahydropyran-2-yl]methyl acetate

Product 1

HCID 671974083-(4-bromophenylmethyl)-4-methyl-1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indoleYield 67.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Add manganese (IV) oxide (172.5 mmol) to a solution of [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[(4-bromophenyl)methyl]-4-methyl-indolin-1-yl]tetrahydropyran-2-yl]methyl acetate (5.85 mmol) in dichloromethane (20 mL). Stir at room temperature for 48 hours. Filter the reaction through diatomaceous earth and concentrate under reduced pressure. Treat the crude product with dichloromethane/methanol (30 mL of 10:1) and stir for 15 minutes. Filter the resulting precipitate and rinse the filter cake with methanol (2×10 mL). Dry the filter cake under vacuum to yield the title compound as a colorless solid (2.5 g 3.97 mmol): MS (m/z): 630 (M+H).

Workup

  1. filtrationFilter
  2. customthe reaction through diatomaceous earth
  3. concentrationconcentrate under reduced pressure
  4. additionTreat the crude product with dichloromethane/methanol (30 mL of 10:1)
  5. stirringstir for 15 minutes
  6. filtrationFilter the resulting precipitate
  7. washrinse the filter cake with methanol (2×10 mL)
  8. customDry the filter cake under vacuum

Sources & evidence

ORD record
ord-9b815b3661f04e118ab10f29d177ec91
Source dataset
uspto-grants-2015_09
Patent number
US09145435B2

Reaction notes

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