Ethyl Acetate → D-(+)-Glucal

HRID 1967179Notes

Reaction equation

HRID 1967179 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([CH2:15][O:16]C(=O)C)[O:8][CH:7]=[CH:6]1)(=O)C.C[O-].[Na+].CCOC(C)=O>CO>[O:8]1[C@H:9]([CH2:15][OH:16])[C@@H:10]([OH:11])[C@H:5]([OH:4])[CH:6]=[CH:7]1

Participants

5

Reactant 3

HCID 8857Ethyl Acetate2×HCID 688303Tri-O-acetyl-D-glucalHCID 10942334Sodium Methoxide

Product 1

HCID 2734736D-(+)-Glucal

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The Tri-O-Acetyl-D-Glucal [SM-A] (100 g, 367 mmol) is dissolved in dry MeOH [1.5 L], and then NaOMe (110 mmol, 5.95 g) is added into reaction mixture. Within about 20 minutes, TLC (40% EtOAc/60% hexanes & 100% EtOAc) confirmed de-acetylated glucal. The reaction is quenched with 50WX4 cation exchange resin until pH is near 7.0 by pH strip paper. The mixture is filtered and evaporated to dryness under vacuum to yield syrupy glucal intermediate IntA1 (59 g). Theoretical yield=100 g×(146/272)=53.7 g TLC IntA1Rf=0.1, SiO2, 100% Ethyl Acetate

Workup

  1. customThe reaction is quenched with 50WX4 cation exchange resin until pH
  2. filtrationThe mixture is filtered
  3. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-391204e2e89e4e058d2cdd3364b6aae4
Source dataset
uspto-grants-2013_04
Patent number
US08420790B2

Reaction notes

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