Ethyl Acetate → HCID 2723959, compound

HRID 2408167Notes

Reaction equation

HRID 2408167 reaction equation
C[O-].[Na+].C([O:7][C@@H:8]1[C@H:17]([O:18]CC2C=CC=CC=2)[C@@H:16]([O:26]CC2C=CC=CC=2)[C@H:15]([CH3:34])[O:14][C@H:9]1[O:10]CC=C)(=[O:6])C.CCOC(C)=O>CO>[CH3:34][C@@H:15]1[O:14][CH:9]([OH:10])[C@H:8]([OH:7])[C@H:17]([OH:18])[C@H:16]1[OH:26].[OH2:6]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 67541659HCID 67541659, compound2×

Product 1

HCID 2723959HCID 2723959, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After adding 0.5 M NaOMe (222.7 mL, 111.0 mmol, 1 eq.) to the allyl glycoside 76 (47.5 g, 111.0 mmol) in solution in MeOH (150 mL), the reaction mixture is stirred for 2 h and its development is monitored by TLC (Chex/EtOAc, 7/3). After observing the disappearance of 76 (Rf=0.6) and the appearance of a more polar product (Rf=0.35), the reaction mixture is neutralized by adding DOWEX (H+) ion-exchange resin, then filtered on a frit. The resin is washed with DCM/MeOH mixture and the solvents are evaporated. The yellow oil obtained is purified by silica gel chromatography (Chex/EtOAc, 8/2→7/3) to give the alcohol 58 in the form of a colorless oil (39.2 g, 92% or 61% starting from commercial L-rhamnose 27).

Workup

  1. additionby adding DOWEX (H+) ion-exchange resin
  2. filtrationfiltered on a frit
  3. washThe resin is washed with DCM/MeOH mixture
  4. customthe solvents are evaporated
  5. customThe yellow oil obtained
  6. customis purified by silica gel chromatography (Chex/EtOAc, 8/2→7/3)

Sources & evidence

ORD record
ord-db36c93a695446a9b26193ff4c8e6698
Source dataset
uspto-grants-2014_08
Patent number
US08815239B2

Reaction notes

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