DL-Arabinose → Furaneol

HRID 1886196Notes

Reaction equation

HRID 1886196 reaction equation
C(O)C(O)C(O)C(O)C=O.[CH3:11][CH:12]([OH:21])[CH:13]([OH:20])[CH:14]([OH:19])[CH:15](O)[CH:16]=O.O=C[C@@H]([C@@H]([C@H]([C@H](C)O)O)O)O.C(O)(=O)C.N1CCCCC1>C(O)C>[CH3:16][CH:15]1[C:14](=[O:19])[C:13]([OH:20])=[C:12]([CH3:11])[O:21]1

Participants

6

Reactant 4

HCID 854DL-ArabinoseHCID 19233(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanalHCID 2200016-DeoxyhexoseHCID 9793820Piperidine, acetate

Product 1

HCID 19309FuraneolYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Several methods of preparation of these compounds involving a pentose or a 6-deoxyhexose are known: U.S. Pat. No. 2,936,308 (Hodge) discloses the reaction of L-rhamnose and piperidine acetate at 75°C. for 18 hours in ethanol and a 26% yield of 2,5-dimethyl-4-hydroxy-2,3-dihydrofuran-3-one was obtained according to Example 2. Although the desired compound was formed in a reasonable yield, it was contaminated with a nitrogen-containing by-product (2,5-dimethyl-4-piperidino-2,3-dihydrofuran3one), which was difficult to remove. The same preparation is disclosed in GB 1,132,600. GB 1,238,942 discloses the reaction between a pentose or 6-deoxy-aldohexose with a dialkylamine to a glycosylamine which further reacts with acid to form the desired compounds. Before isolating the product from the reaction mixture the solvent is removed by distillation under reduced pressure at a temperature below 35° C. The product is then isolated through extraction with an organic solvent followed by purification through column chromatography.

Workup

  1. customSeveral methods of preparation of these compounds

Sources & evidence

ORD record
ord-1776fb8cc82545b3bb0beb54008a028c
Source dataset
uspto-grants-1992_09
Patent number
US05149840

Reaction notes

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