(1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol → (3aR,5S,6aR)-2,2-Dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

HRID 60692Notes

Reaction equation

HRID 60692 reaction equation
[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]2[O:7][C@H:8]([C@@H:10]([OH:13])CO)[CH2:9][C@H:4]2[O:3]1.I([O-])(=O)(=O)=O.[Na+]>CO>[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]2[O:7][C@H:8]([CH:10]=[O:13])[CH2:9][C@H:4]2[O:3]1

Participants

4

Reactant 2

HCID 11148396(1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol2×HCID 23667635Sodium periodate

Product 1

HCID 10910018(3aR,5S,6aR)-2,2-Dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehydeYield 90.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1S)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol (compound 1c, 18 g, 90 mmol) in the MeOH (250 mL) cooled in ice bath was added sodium metaperiodate (23.1 g, 108 mmol). After being stirred at room temperature for 12 hours, the resulting suspension was filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:2 EtOAc in petroleum ether) to afford 14 g of (3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde (compound 1d). MS obsd. (ESI+) [(M+NH4)+]: 190.

Workup

  1. filtrationthe resulting suspension was filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 1:2 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-fb75924a51da4741a711925dd63fb896
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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