Potassium Sodium Tartrate → (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydro-2H-pyran-2-ol

HRID 1261815Notes

Reaction equation

HRID 1261815 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:14][C@@H:13]([CH:15]([O:18][CH3:19])[O:16][CH3:17])[O:12][C:11](=[O:20])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>ClCCl.O>[Si:1]([O:8][C@@H:9]1[CH2:14][C@@H:13]([CH:15]([O:16][CH3:17])[O:18][CH3:19])[O:12][CH:11]([OH:20])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 68898127(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one

Product 1

HCID 69184843(4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydro-2H-pyran-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 0.6 g of (4R,6S)-4-(tert-butyldimethylsilyloxy)-6-(dimethoxymethyl)-tetrahydropyran-2-one (III′) in 36 mL of dichloromethane is cooled to −78° C. after 2 mL of DIBALH (25% in toluene) are added over 10 minutes. After 1 hour of stirring at −78° C., 0.9 g of Rochelle salt in 60 mL of water are added, phases are separated and dichloromethane is distilled off. The residue is flash chromatographed (MTBE/hexane 1/1) and the solvents are distilled off to get the title compound.

Workup

  1. additionare added over 10 minutes
  2. customphases are separated
  3. distillationdichloromethane is distilled off
  4. customchromatographed (MTBE/hexane 1/1)
  5. distillationthe solvents are distilled off

Sources & evidence

ORD record
ord-4510e041ad1c4ddf8fdd83731bb502e8
Source dataset
uspto-grants-2013_06
Patent number
US08471045B2

Reaction notes

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