Sodium Bicarbonate → (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

HRID 60691Notes

Reaction equation

HRID 60691 reaction equation
CC1(C)[O:6][CH:5]([C@H:7]2[O:16][C@@H:10]3[O:11][C:12]([CH3:15])([CH3:14])[O:13][C@@H:9]3[CH2:8]2)[CH2:4][O:3]1.C([O-])(O)=O.[Na+]>CC(O)=O.O>[CH3:14][C:12]1([CH3:15])[O:11][C@H:10]2[O:16][C@H:7]([C@@H:5]([OH:6])[CH2:4][OH:3])[CH2:8][C@H:9]2[O:13]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 134792743-Deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose2×

Product 1

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-diolYield 62.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of (3aR,5S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole (compound 1b, 10.0 g, 40.9 mmol) in 60% HOAc in water (20 mL) was stirred at 40° C. for 16 hours. The reaction mixture was adjusted to pH 8˜8.5 by saturated NaHCO3 solution and extracted with EtOAc. The organic layer was combined and concentrated, the residue was purified by column chromatography on silica gel (eluting with 1:2 EtOAc in petroleum ether) to afford 5.2 g 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). MS obsd. (ESI+) [(M+NH4)+]: 222.

Workup

  1. extractionextracted with EtOAc
  2. concentrationconcentrated
  3. customthe residue was purified by column chromatography on silica gel (eluting with 1:2 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-4c9c17de93f449bd8821896465b1007a
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

Loading…