Acetone → 30725-00-9

HRID 1165554Notes

Reaction equation

HRID 1165554 reaction equation
[C:1]1(=[O:10])[O:9][C@H:6]([CH2:7][OH:8])[C@H:4]([OH:5])[C@@H:2]1[OH:3].[CH3:11][C:12]([CH3:14])=O>>[CH3:11][C:12]1([CH3:14])[O:3][CH:2]2[CH:4]([CH:6]([CH2:7][OH:8])[O:9][C:1]2=[O:10])[O:5]1

Participants

3

Reactant 2

HCID 180AcetoneHCID 11829598HCID 11829598, compound

Product 1

HCID 50017230725-00-9

Procedure

The multi-step synthesis from D-galactose comprises oxidizing the D-galactose in KOH solution to open the pyranose ring and form potassium D-lyxonate, subjecting the latter compound to alcoholic solution under acid conditions to provide furanose ring closure and form the D-lyxono-1,4-lactone, and then introducing a protecting group at C-2 and C-3 by reaction with ketone in the presence of a dehydrating agent. Use of acetone as the ketone in the latter step gives the compound 2,3-0-isopropylidene-D-lyxono-1,4-lactone. From that point on the multi-step system includes the general reaction steps of the above short synthesis.

Workup

  1. customto provide furanose ring closure
  2. additionintroducing a protecting group at C-2 and C-3

Sources & evidence

ORD record
ord-1c72f21cb8374379831068821cddb6b7
Source dataset
uspto-grants-1990_03
Patent number
US04910310

Reaction notes

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