Triacetoxyperiodinane → HCID 86635715, compound

HRID 1697263Notes

Reaction equation

HRID 1697263 reaction equation
[Si:1]([O:8][C@H:9]([CH2:32][OH:33])[C@@H:10]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[C:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Si:1]([O:8][C@H:9]([CH:32]=[O:33])[C@@H:10]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[C:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86635714HCID 86635714, compound

Product 1

HCID 86635715HCID 86635715, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A RBF containing a solution of tert-butyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-1-(3-(2-(trimethylsilyl)ethynyl)phenyl)butan-2-ylcarbamate (2.04 g, 4.15 mmol) in DCM (30 mL) was placed in an ice-bath for 10 min. Sodium bicarbonate (1.05 g, 12.4 mmol) and Dess-Martin Periodinane (2.29 g, 5.39 mmol) were added in sequence, the ice-bath was removed, and the reaction was stirred for 2 h. The reaction mixture was diluted with a 1:1 mixture of saturated sodium thiosulfate solution and brine (60 mL), and the resulting biphasic mixture was stirred vigorously for 2 min. The mixture was then extracted with DCM (3×30 mL), and the combined organic extracts were dried over sodium sulfate, filtered, and evaporated. The residue was purified by chromatography on a 120-g Redi-Sep column, eluting with 5-30% EtOAc/Hexanes to give tert-butyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-4-oxo-1-(3-(2-(trimethylsilyl)ethynyl)phenyl)butan-2-ylcarbamate as a pale yellow oil.

Workup

  1. customthe ice-bath was removed
  2. additionThe reaction mixture was diluted with a 1:1 mixture of saturated sodium thiosulfate solution and brine (60 mL)
  3. stirringthe resulting biphasic mixture was stirred vigorously for 2 min
  4. extractionThe mixture was then extracted with DCM (3×30 mL)
  5. dry with materialthe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography on a 120-g Redi-Sep column
  9. washeluting with 5-30% EtOAc/Hexanes

Sources & evidence

ORD record
ord-6569c32a01c84f4c89e395fe49f903b3
Source dataset
uspto-grants-2012_04
Patent number
US08163909B2

Reaction notes

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