95-44-3

Usage

Uses

Used in Pharmaceutical Industry:
L-(+)-THREOSE is used as a pharmaceutical ingredient for its ability to glycate and crosslink lens proteins, which can be utilized in the development of treatments for various health conditions.
Used in Nutritional Supplements:
L-(+)-THREOSE is used as a nutritional supplement due to its association with ascorbic acid, which is an essential nutrient for the human body.
Used in Cosmetics Industry:
L-(+)-THREOSE is used as a cosmetic ingredient for its potential to improve skin health and appearance by promoting collagen production and reducing the signs of aging.
Used in Food and Beverage Industry:
L-(+)-THREOSE is used as a natural sweetener and flavor enhancer in the food and beverage industry, providing a unique taste and texture to various products.
Used in Research and Development:
L-(+)-THREOSE is used as a research compound for studying the degradation of ascorbic acid and its potential applications in various fields, including pharmaceuticals, cosmetics, and food science.

InChI:InChI=1/C4H8O4/c5-2-1-8-4(7)3(2)6/h2-7H,1H2/t2?,3?,4-/m0/s1

Upstream product

• 34693-27-1 (3aR,6S,6aR)-6-hydroxy-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole 
• 50-81-7 ascorbic acid 
• 96-26-4 dihydroxyacetone 
• 141-46-8 Glycolaldehyde 
• 608-66-2 D-galactitol 
• 7732-18-5 water 
• 14694-95-2 Wilkinson's catalyst 
• 533-50-6 L-erythrulose 
• 50-00-0 formaldehyd 
• 23147-58-2 glycolaldehyde dimer 
• 909878-64-4 meso-erythritol 

Downstream Products

• 87-79-6 L-sorbose 
• 2319-57-5 threitol 
• 3154-37-8 3,4-dihydroxy-2-phenylhydrazono-butyraldehyde phenylhydrazone 
• 57-48-7 sorbose 
• 781577-54-6 calcium(II) oxalate 
• 5892-21-7 calcium mesotartrate*3H₂O 
• 18952-67-5 Erythrose-methylphenylalkazon; Tetraoxo-butan-tetrakis-(1-methyl-1-phenyl-hydrazon) 
• 2319-57-5 1,2,3,4-butanetetrol 

Relevant academic research and scientific papers

Selective Reductive Dimerization of CO2into Glycolaldehyde

The selective dimerization of CO2 into glycolaldehyde is achieved in a one-pot two-step process via formaldehyde as a key intermediate. The first step concerns the iron-catalyzed selective reduction of CO2 into formaldehyde via formation and controlled hydrolysis of a bis(boryl)acetal compound. The second step concerns the carbene-catalyzed C-C bond formation to afford glycolaldehyde. Both carbon atoms of glycolaldehyde arise from CO2 as proven by the labeling experiment with 13CO2. This hybrid organometallic/organic catalytic system employs mild conditions (1 atm of CO2, 25 to 80 °C in less than 3 h) and low catalytic loadings (1 and 2.5%, respectively). Glycolaldehyde is obtained in 53% overall yield. The appealing reactivity of glycolaldehyde is exemplified (i) in a dimerization process leading to C4 aldose compounds and (ii) in a tri-component Petasis-Borono-Mannich reaction generating C-N and C-C bonds in one process.

Shape-selective Valorization of Biomass-derived Glycolaldehyde using Tin-containing Zeolites

A highly selective self-condensation of glycolaldehyde to different C4 molecules has been achieved using Lewis acidic stannosilicate catalysts in water at moderate temperatures (40–100 °C). The medium-sized zeolite pores (10-membered ring framework) in Sn-MFI facilitate the formation of tetrose sugars while hindering consecutive aldol reactions leading to hexose sugars. High yields of tetrose sugars (74 %) with minor amounts of vinyl glycolic acid (VGA), an α-hydroxyacid, are obtained using Sn-MFI with selectivities towards C4 products reaching 97 %. Tin catalysts having large pores or no pore structure (Sn-Beta, Sn-MCM-41, Sn-SBA-15, tin chloride) led to lower selectivities for C4 sugars due to formation of hexose sugars. In the case of Sn-Beta, VGA is the main product (30 %), illustrating differences in selectivity of the Sn sites in the different frameworks. Under optimized conditions, GA can undergo further conversion, leading to yields of up to 44 % of VGA using Sn-MFI in water. The use of Sn-MFI offers multiple possibilities for valorization of biomass-derived GA in water under mild conditions selectively producing C4 molecules.

Catalytic effect of aluminium chloride on the example of the conversion of sugar model compounds

Abstract In this work, the catalytic effect of the Bronsted acid hydrochloric acid, the Bronsted base sodium hydroxide and the Lewis acid AlCl3 on the conversion of biomass derived carbohydrates is investigated. On the example of the glycolaldehyde conversion, it is shown that the Lewis acid catalyses the ketol-endiol-tautomerism, the dehydration, the retro-aldol-reaction and the benzilic-acid-rearrangement. The main products are C4- and C6-carbohydrates as well as their secondary products 2-hydroxybut-3-enoic acid 1 and several furans. Under the same reaction conditions hydrochloric acid catalyzes mainly the dehydration and sodium hydroxide the tautomerism and subsequent aldolization.

Asymmetric organocatalytic formation of protected and unprotected tetroses under potentially prebiotic conditions

Esters of proteinogenic amino acids efficiently catalyse the formation of erythrose and threose under potentially prebiotic conditions in the highest yields and enantioselectivities yet reported. Remarkably while esters of (l)-proline yield (l)-tetroses, esters of (l)-leucine, (l)-alanine and (l)-valine generate (d)-tetroses, offering the potential to account for the link between natural (l)-amino acids and natural (d)-sugars. The effect of pH and NaCl on the yields and enantioselectivities was also investigated and was shown to be significant, with the optimal enantioselectivities occurring at pH 7.

Rhodium-catalyzed decarbonylation of aldoses

(Chemical Equation Presented) A catalytic procedure is described for decarbonylation of unprotected aldoses to afford alditols with one less carbon atom. The reaction is performed with the rhodium complex Rh(dppp)2Cl in a refluxing diglyme-DMA solution. A slightly improved catalyst turnover is observed when a catalytic amount of pyridine is added. Under these conditions most hexoses and pentoses undergo decarbonylation into the corresponding pentitols and tetrols in isolated yields around 70%. The reaction has been applied as the key transformation in a five-step synthesis of L-threose from D-glucose.

Methods for the electrolytic production of erythrose or erythritol

Methods for the production of erythrose and/or erythritol are provided herein. Preferably, the methods include the step of electrolytic decarboxylation of a ribonic acid or arabinonic acid reactant to produce erythrose. Optionally, the reactant can be obtained from a suitable hexose sugar, such as allose, altrose, glucose, fructose or mannose. The erythrose product can be hydrogenated to produce erythritol.

Metal-mediated decarbonylation and dehydration of ketose sugars

Ketose sugars can be decarbonylated and/or dehydrated by the action of certain metal complexes. Fructose reacts with 1 equiv of RhCl(PPh3)3 (1) in N-methyl-2-pyrrolidinone (NMP) at 130°C to give furfuryl alcohol, Rh(CO)Cl(PPh3)2 (2), and a small amount of 1-deoxyerythritol. 1,3-Dihydroxyacetone consumes 2 equiv of 1, giving methane and ca. 2 mol of 2. With manno-2-heptulose the primary product is 2,7-anhydromanno-2-heptulopyranose. The mechanisms of these unusual reactions have been studied by using 13C-labeling experiments and model reactions employing Pd(II) and HCl. Attempts to make the reactions catalytic using [Rh(Ph2PCH2CH2CH2PPh 2)2]+[BF4]- in place of 1 were not successful. The use of NMP as a solvent offers some advantages in the acid-catalyzed synthesis of certain carbohydrate dehydration products, as exemplified by the conversion of manno-2-heptulose to its 2,7-anhydride and of 2-deoxyglucose to 1-(2-furanyl)-1,2-ethanediol.

NOVEL SYNTHETIC EQUIVALENTS OF DIFFERENTIALLY PROTECTED TARTARIC ALDEHYDES. A SIMPLE ROUTE TO USEFUL C-4 CHIRAL SYNTHONS.

The synthesis of 4-acetoxy-3-O-benzyl-1,2-O-isopropylidene aldotetroses from D-glucose is reported.These synthetic equivalents of tartaric aldehydes are chemoselectively reduced at the acetoxylated center leading to a series of useful differentially protected C-4 chiral synthons.

Kinetics, Catalysis, and Mechanism of the Secondary Reaction in the Final Phase of the Formose Reaction

In the final phase of the formose reaction sugars are formed by the reaction of glycolaldehyde, glyceraldehyde and dihydroxyacetone.The application of high-pressure liquid chromatography allows for the first time to investigate intermediate and final products quantitatively.The results of kinetical investigations allow to suggest a reaction mechanism for the secondary reaction in the final phase of the formose reaction.This mechanism is compared with that of the starting phase and other known mechanisms.From the results metal ion-catalyzed aldol reactions have to be assumed.