Sodium Thiosulfate → HCID 57515882, compound

HRID 1921962Notes

Reaction equation

HRID 1921962 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:12]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:13][C:14]#[C:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH2:10][OH:11])([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)C2C1=CC=CC=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Si:1]([O:8][C@@H:9]([C@@H:12]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:13][C:14]#[C:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:10]=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57515881HCID 57515881, compound

Product 1

HCID 57515882HCID 57515882, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2S,3S)-2-(tert-butyldimethylsilyloxy)-1-hydroxy-6-(trimethylsilyl)hex-5-yn-3-ylcarbamate (1.83 g, 4.4 mmol) in DCM (20 mL) were added sodium bicarbonate-(1.5 g, 18 mmol) and Dess-MartinPeriodinane (2.4 g, 5.7 mmol) and the reaction was stirred at rt for 1 h. The mixture was quenched with sat NaHCO3 followed by the addition of sodium thiosulfate (3.5 g, 22 mmol) and stirred for an additional 1 h. The reaction was extracted with DCM and the combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated to afford a light yellow oil as tert-butyl (2S,3S)-2-(tert-butyldimethylsilyloxy)-1-oxo-6-(trimethylsilyl)hex-5-yn-3-ylcarbamate. MS m/z: 316.2 (M+1).

Workup

  1. customThe mixture was quenched with sat NaHCO3
  2. stirringstirred for an additional 1 h
  3. extractionThe reaction was extracted with DCM
  4. washthe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-37a00b60083d48a69de880ecda5f48a6
Source dataset
uspto-grants-2012_05
Patent number
US08173810B2

Reaction notes

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