Sodium borohydride → HCID 54187910, compound

HRID 1587473Notes

Reaction equation

HRID 1587473 reaction equation
[CH:1]1([O:12][CH2:13][C:14]2[CH:20]=[CH:19]OC=2C=O)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[BH4-].[Na+]>CO>[C@H:1]1([O:12][CH2:13][C:14]2[O:3][C:2]([CH2:1][OH:9])=[CH:19][CH:20]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18652369HCID 18652369, compound2×

Product 1

HCID 54187910HCID 54187910, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

520 mg (1.8 mmol) glucosyloxymethylfurfural (formula 2, product of Example 1) was dissolved in 30 ml methanol, and 138 mg (3.6 mmol) sodium borohydride added. After stirring for 2 h at room temperature the thin-layer chromatogram showed no further educt. To work up the product, the solvent was removed under vacuum and the syrup remaining purified by elution with chloroform/methanol (3:1). After evaporation of the fractions 443 mg (85%) glucosyloxymethylhydroxymethylfuran of formula (3) remained as a colourless syrup with [α]D20 =+107° (c=1, methanol).

Workup

  1. customthe solvent was removed under vacuum
  2. customthe syrup remaining purified by elution with chloroform/methanol (3:1)
  3. customAfter evaporation of the fractions 443 mg (85%) glucosyloxymethylhydroxymethylfuran of formula (3)
  4. customremained as a colourless syrup with [α]D20 =+107° (c=1, methanol)

Sources & evidence

ORD record
ord-be1c8fadf90a4728900c797c3a194eb0
Source dataset
uspto-grants-1993_06
Patent number
US05218098

Reaction notes

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