Triacetoxyperiodinane → (3aS,6R,6aS)-6-(tert-butyldimethylsilyloxy)tetrahydrofuro[3,2-b]furan-3(2H)-one

HRID 2168174Notes

Reaction equation

HRID 2168174 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([Si:27]([CH3:39])([CH3:38])[O:28][C@H:29]1[C@H:33]2[O:34][CH2:35][C@@H:36]([OH:37])[C@H:32]2[O:31][CH2:30]1)([CH3:26])([CH3:25])[CH3:24]>ClCCl>[Si:27]([O:28][C@H:29]1[C@H:33]2[O:34][CH2:35][C:36](=[O:37])[C@H:32]2[O:31][CH2:30]1)([C:23]([CH3:26])([CH3:24])[CH3:25])([CH3:39])[CH3:38]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67050109(3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol

Product 1

HCID 67049238(3aS,6R,6aS)-6-(tert-butyldimethylsilyloxy)tetrahydrofuro[3,2-b]furan-3(2H)-oneYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
32.5 °C

Procedure

Dess-Martin periodinane (31.18 g, 73.5 mmol) was added to a stirred solution of alcohol (86) (9.56 g, 36.8 mmol) in dichloromethane (110 mL) under an atmosphere of argon. The mixture was stirred at 30-35° C. for 5 hours, at ambient temperature for 16 hours, at 30-35° C. for 8 hours and at ambient temperature for 20 hours before adding Isolute® HM-N then removing the solvents in vacuo. Flash chromatography over silica, eluting with ethyl acetate:heptane mixtures 5:95 to 40:60 gave ketone (87) as a pale yellow oil (8.62 g, 91%).

Workup

  1. additionbefore adding Isolute® HM-N
  2. customthen removing the solvents in vacuo
  3. washFlash chromatography over silica, eluting with ethyl acetate

Sources & evidence

ORD record
ord-93b8a535f7844fc3b5eec49d54e306a7
Source dataset
uspto-grants-2015_06
Patent number
US09045492B2

Reaction notes

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