Preparation of l-lyxose and some of its furanose derivatives

Kuzuhara, Hiroyoshi; Terayama, H; Ohrui, Hiroshi; Emoto, Sakae

doi:10.1016/s0008-6215(00)84958-7

Cited by 13 publications

(4 citation statements)

References 9 publications

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“…It should be pointed out that under these isopropylidenation conditions, d-lyxose furnished only its ,-2,3-O-isopropylidenefuranose (Barbat et al, 1991). Compound 1 was previously obtained starting from d-glucose via d-gulose (Kuzuhara et al, 1971). The scarcity of any experimental data on 1 prompted us to examine its structure.…”

Section: Structure Descriptionmentioning

confidence: 99%

1,2-O-Isopropylidene-β-D-lyxo-furanose

Doboszewski¹,

Nazarenko²

2020

IUCr Data

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In the title compound C8H14O5, the pentofuranose five-membered ring has a twisted conformation on two carbon atoms while the five-membered ring of the isopropylidene group has an envelope conformation on an oxygen atom. Hydroxy groups are involved an infinite network of O—H...O hydrogen bonds that leads to the formation of a layer parallel to the (001) plane. Only weak C—H...O contacts exist between neighboring layers.

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Section: Structure Descriptionmentioning

confidence: 99%

1,2-O-Isopropylidene-β-D-lyxo-furanose

Doboszewski¹,

Nazarenko²

2020

IUCr Data

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“…L-lyxose is very expensive due to its scarcity in nature and it can be obtained only by chemical synthesis (Whistler and BeMiller, 1962;Kazuhara et al 1971;Bilk and Caplovic, 1973;Petrusova et al 1991). In a previous study, Bhuiyan et al (1998) reported an enzyme biotrasformation of L-lyxose from ribitol, where the complete biotransformation of ribitol to L-ribulose was achieved using A. aceti IFO 3281 at high substrate concentrations ranging from 5-20% and then Lribulose was used as a starting substrate.…”

Section: L-lyxose Productionmentioning

confidence: 99%

Production of natural and rare pentoses using microorganisms and their enzymes

Ahmed¹

2001

Electron. J. Biotechnol.

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“…However, the yield for this method was low (<13%). Kuzuhara et al 5 improved the synthesis method of Llyxose by starting from a cheaper chemical, D-glucose, but the overall yield was only 30%. Brimacombe et al 6 used 1,2:5,6di-O-isopropylidene-a-D-gulofuranose as the starting material to produce L-lyxose.…”

Section: Introductionmentioning

confidence: 99%

A heterogeneous Pd–Bi/C catalyst in the synthesis of l-lyxose and l-ribose from naturally occurring d-sugars

2011

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A critical step in the synthesis of the rare sugars, L-lyxose and L-ribose, from the corresponding D-sugars is the oxidation to the lactone. Instead of conventional oxidizing agents like bromine or pyridinium dichromate, it was found that a heterogeneous catalyst, Pd-Bi/C, could be used for the direct oxidation with molecular oxygen. The composition of the catalyst was optimized and the best results were obtained with 5 : 1 atomic ratio of Pd : Bi. The overall yields of the five-step procedure to L-ribose and L-lyxose were 47% and 50%, respectively. The synthetic procedure is advantageous from the viewpoint of overall yield, reduced number of steps, and mild reaction conditions. Furthermore, the heterogeneous oxidation catalyst can be easily separated from the reaction mixture and reused with no loss of activity.

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Preparation of l-lyxose and some of its furanose derivatives

Cited by 13 publications

References 9 publications

1,2-O-Isopropylidene-β-D-lyxo-furanose

1,2-O-Isopropylidene-β-D-lyxo-furanose

Production of natural and rare pentoses using microorganisms and their enzymes

A heterogeneous Pd–Bi/C catalyst in the synthesis of l-lyxose and l-ribose from naturally occurring d-sugars

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