4573-78-8

Usage

Uses

Used in Pharmaceutical Industry:
D-HAMAMELOSE is used as a binding agent for the human Intelectin-1 protein, which plays a crucial role in the immune system. This interaction could modulate the binding of other protein ligands, potentially leading to the development of new therapeutic agents.
Used in Chemical Synthesis:
D-HAMAMELOSE is used as a reagent in the synthesis of Trachycladines A/B and their analogues. These compounds have shown promising biological activities, making them valuable targets for drug discovery and development.

InChI:InChI=1/C6H12O6/c7-1-4(10)5(11)6(12,2-8)3-9/h2,4-5,7,9-12H,1,3H2/t4-,5-,6-/m1/s1

Upstream product

• 57-48-7 D-Fructose 
• 96-26-4 dihydroxyacetone 
• 56-82-6 Glyceraldehyde 
• 141-46-8 Glycolaldehyde 

Downstream Products

• 97-64-3 ethyl 2-hydroxypropionate 

Relevant academic research and scientific papers

PRODUCTION OF ALPHA-HYDROXY CARBOXYLIC AIDS AND ESTERS FROM HIGHER SUGARS USING TANDEM CATALYST SYSTEMS

The present disclosure is directed to methods and composition used in the preparation of alpha-hydroxy carboxylic acids and esters from higher sugars using a tandem catalyst system comprising retro-aldol catalysts and Lewis acid catalysts. In some embodiments, these alpha-hydroxy carboxylic acids may be prepared from pentoses and hexoses. The retro-aldol and Lewis catalysts may be characterized by their respective ability to catalyze a 1,2-carbon shift reaction and a 1,2-hydride shift reaction on an aldose or ketose substrate.

Stereospecific molybdic acid-catalyzed isomerization of 2-hexuloses to branched-chain aldoses

On treatment with a catalytic amount of molybdic acid in aqueous solution, the 2-ketohexoses D-fructose, L-sorbose and D-tagatose undergo a stereospecific intramolecular rearrangement to give the corresponding 2-C-(hydroxymethyl)aldoses, 2-C-(hydroxymethyl)-D-ribose (D-hamamelose), 2-C-(hydroxymethyl)-L-lyxose, and 2-C-(hydroxymethyl)-D-xylose, respectively. At equilibrium, the ratio of 2-ketose to 2-C-(hydroxymethyl)aldose ranged from 14:1 (fructose) to 32:1 (sorbose). A similar treatment of D-psicose failed to yield a significant amount of the corresponding branched-chain aldose. The equilibria can be shifted with the addition of boric acid to the reaction mixture; under these conditions, ratios of 3:1 and 7:1 were obserwed for D-fructose and L-sorbose, respectively. A mechanistic study with D-(3-13C)fructose afforded D-(1-13C)hamamelose, thus confirming C-3 - C-4 bond cleavage with concomitant C-2 - C-3 transposition suggested from recent studies with D-(2-13C)fructose. Copyright (C) 1999 Elsevier Science Ltd.

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.