Trimethylsilyl iodide → (2S,3R,4R,5S,6R)-2-(4-Chloro-3-((7-methylbenzo[e][1,2,4]triazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

HRID 46211Notes

Reaction equation

HRID 46211 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C@H:20]2[C@H:25]([O:26]CC3C=CC=CC=3)[C@@H:24]([O:34]CC3C=CC=CC=3)[C@H:23]([O:42]CC3C=CC=CC=3)[C@@H:22]([CH2:50][O:51]CC3C=CC=CC=3)[O:21]2)=[CH:16][C:3]=1[CH2:4][C:5]1[N:6]=[N:7][C:8]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:9]=2[N:10]=1.[Si](I)(C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([C@H:20]2[C@H:25]([OH:26])[C@@H:24]([OH:34])[C@H:23]([OH:42])[C@@H:22]([CH2:50][OH:51])[O:21]2)=[CH:16][C:3]=1[CH2:4][C:5]1[N:6]=[N:7][C:8]2[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:9]=2[N:10]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 67288325HCID 67288325, compound

Product 1

HCID 49847251(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((7-methylbenzo[e][1,2,4]triazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)-7-methylbenzo[e][1,2,4]triazine (115 mg, 0.15 mmol) in acetonitrile (10 ml) reacted with TMSI (146 mg, 0.73 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 day. After quenching the reaction with methanol, solvent was evaporated under reduced pressure. The residue was purified with silica gel (10% MeOH in CH2Cl2) to afford title compound (33 mg, 52% yield) as a light yellow solid.

Workup

  1. customAfter quenching
  2. customthe reaction with methanol, solvent
  3. customwas evaporated under reduced pressure
  4. customThe residue was purified with silica gel (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-0a186fe7792143bfadfb9ed859242fb3
Source dataset
uspto-grants-2013_09
Patent number
US08541380B2

Reaction notes

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