13074-06-1

Basic information

• Product Name: 6-DEOXY-L-GALACTITOL
• Synonyms: 6-DEOXY-L-GALACTITOL;L-FUCITOL;1-Deoxy-D-galactitol;Rhodeitol
• CAS NO: 13074-06-1
• Molecular Formula: C₆H₁₄O₅
• Molecular Weight: 166.17
• Mol File: 13074-06-1.mol

Chemical Properties

• Melting Point: 154-156 °C
• Boiling Point: 468°Cat760mmHg
• Flash Point: 244.3°C
• Appearance: /
• Density: 1.424g/cm³
• Vapor Pressure: 1.01E-10mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 13.58±0.20(Predicted)
• CAS DataBase Reference: 6-DEOXY-L-GALACTITOL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-DEOXY-L-GALACTITOL(13074-06-1)
• EPA Substance Registry System: 6-DEOXY-L-GALACTITOL(13074-06-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13074-06-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-DEOXY-L-GALACTITOL is used as a pharmaceutical compound for its potential therapeutic effects. It may have applications in the development of new drugs due to its unique chemical structure and properties.
Used in Chemical Research:
6-DEOXY-L-GALACTITOL serves as a valuable compound in chemical research, particularly in the study of sugar chemistry, enzymatic reactions, and the development of novel synthetic pathways.
Used in Biochemical Applications:
In the field of biochemistry, 6-DEOXY-L-GALACTITOL can be used to determine the structure and function of enzymes that act on sugars, such as glycosidases and isomerases, by providing a unique substrate for these enzymes.
Used in Food Industry:
6-DEOXY-L-GALACTITOL may have applications in the food industry as a natural sweetener or as an ingredient in the development of new food products, taking advantage of its unique taste and properties.
Used in Cosmetics Industry:
In the cosmetics industry, 6-DEOXY-L-GALACTITOL could be utilized in the formulation of skincare products, potentially offering moisturizing or other beneficial effects due to its sugar alcohol nature.
Used in Material Science:
6-DEOXY-L-GALACTITOL may also find applications in material science, where its unique properties could be exploited in the development of new materials with specific characteristics, such as biodegradable polymers or materials with tailored physical properties.

InChI:InChI=1/C6H14O5/c1-3(8)5(10)6(11)4(9)2-7/h3-11H,2H2,1H3/t3-,4+,5+,6-/m0/s1

Upstream product

• 3615-37-0 D-Fucose 
• 2438-80-4 L-Fucose 
• 5139-39-9 S-ethyl-D-1-thio-galactitol 
• 59-23-4 D-Galactose 
• 5463-33-2 D-galactose-diethyl-dithioacetal 
• 7699-34-5 6-deoxy-D-erythro-[2,5]hexodiulose 
• 7732-18-5 water 
• 73-34-7 6-deoxy-L-galactose 
• 1668-08-2 L-galactono-1,4-lactone 
• 24286-28-0 (3S,4S,5R)-dihydro-3,4-dihydroxy-5-((1'S)-1'-hydroxyethyl)furan-2(3H)-one 
• 1372946-80-9 methyl 6-bromo-6-deoxy-L-galactonate 
• 210100-16-6 6-bromo-6-deoxy-L-galactonolactone 
• 10231-84-2 (4-nitro-phenyl)-α-L-fucopyranoside 
• 6014-42-2 L-rhamnose 

Downstream Products

• 488-28-8 racemic rhodeitol 
• 42927-35-5 ((2S,3R)-2,2-dimethyl-5-((4'R,5'S)-2',2',5'-trimethyl-1',3'-dioxolan-4'-yl)-1,3-dioxolan-4-yl)methanol 
• 7226-60-0 1,2,3,4,5-penta-O-acetyl-L-fucitol 
• 86296-07-3 1-O-trityl-2.3.4.5-tetra-O-acetyl-L-fucitol 
• 42927-36-6 O²,O³;O⁴,O⁵-diisopropylidene-O⁶-(toluene-4-sulfonyl)-D-1-deoxy-galactitol 
• 123594-91-2 (6S)-1-deoxy-D-galactitol 6-(9-anthroate) 2,3,4,5-tetra-p-methoxycinnamate 
• 170452-37-6 2,3,4,5-tetra-O-benzoyl-L-fucitol 
• 170452-38-7 2,3,4,5-tetra-O-benzoyl-aldehydo-L-fucose 

Relevant articles and documents

Designer α1,6-Fucosidase Mutants Enable Direct Core Fucosylation of Intact N-Glycopeptides and N-Glycoproteins

Core fucosylation of N-glycoproteins plays a crucial role in modulating the biological functions of glycoproteins. Yet, the synthesis of structurally well-defined, core-fucosylated glycoproteins remains a challenging task due to the complexity in multistep chemical synthesis or the inability of the biosynthetic α1,6-fucosyltransferase (FUT8) to directly fucosylate full-size mature N-glycans in a chemoenzymatic approach. We report in this paper the design and generation of potential α1,6-fucosynthase and fucoligase for direct core fucosylation of intact N-glycoproteins. We found that mutation at the nucleophilic residue (D200) did not provide a typical glycosynthase from this bacterial enzyme, but several mutants with mutation at the general acid/base residue E274 of the Lactobacillus casei α1,6-fucosidase, including E274A, E274S, and E274G, acted as efficient glycoligases that could fucosylate a wide variety of complex N-glycopeptides and intact glycoproteins by using α-fucosyl fluoride as a simple donor substrate. Studies on the substrate specificity revealed that the α1,6-fucosidase mutants could introduce an α1,6-fucose moiety specifically at the Asn-linked GlcNAc moiety not only to GlcNAc-peptide but also to high-mannose and complex-type N-glycans in the context of N-glycopeptides, N-glycoproteins, and intact antibodies. This discovery opens a new avenue to a wide variety of homogeneous, core-fucosylated N-glycopeptides and N-glycoproteins that are hitherto difficult to obtain for structural and functional studies.

Water-soluble constituents of caraway: aromatic compound, aromatic compound glucoside and glucides.

From the water-soluble portion of the methanolic extract of caraway (fruit of Carum carvi L.), an aromatic compound, an aromatic compound glucoside and a glucide were isolated together with 16 known compounds. Their structures were clarified as 2-methoxy-2-(4'-hydroxyphenyl)ethanol, junipediol A 2-O-beta-D-glucopyranoside and L-fucitol, respectively.

Isomerization of deoxyhexoses: green bioproduction of 1-deoxy-d-tagatose from l-fucose and of 6-deoxy-d-tagatose from d-fucose using Enterobacter agglomerans strain 221e

1-Deoxy-d-tagatose was produced by the hydrogenation of 6-deoxy-l-galactose (l-fucose) to l-fucitol followed by oxidation with Enterobacter agglomerans 221e; a similar sequence on d-fucose afforded 6-deoxy-d-tagatose. Thus, the polylol dehydrogenase recognizes the d-galacto-configuration of both d-fucitol and l-fucitol. The procedures were conducted in water and show the power of green, environmentally friendly biotechnology in the preparation of new monosaccharides with a potential for novel bioactive properties. 6-Deoxy-d-tagatose was also synthesized from d-tagatose via the efficient formation of 1,2:3,4-di-O-isopropylidene-α-d-tagatofuranose; a difficult final removal of protecting groups by acid makes the biotechnological route more attractive.

Boronic acid recognition of non-interacting carbohydrates for biomedical applications: Increasing fluorescence signals of minimally interacting aldoses and sucralose

To address carbohydrates that are commonly used in biomedical applications with low binding affinities for boronic acid based detection systems, two chemical modification methods were utilized to increase sensitivity. Modified carbohydrates were analyzed

Modulating Electrostatic Interactions in Ion Pair Intermediates To Alter Site Selectivity in the C?O Deoxygenation of Sugars

Controlling which products one can access from the predefined biomass-derived sugars is challenging. Changing from CH2Cl2 to the greener alternative toluene alters which C?O bonds in a sugar are cleaved by the tris(pentafluorophenyl)borane/HSiR3 catalyst system. This increases the diversity of high-value products that can be obtained through one-step, high-yielding, catalytic transformations of the mono-, di-, and oligosaccharides. Computational methods helped identify this non-intuitive outcome in low dielectric solvents to non-isotropic electrostatic enhancements in the key ion pair intermediates, which influence the reaction coordinate in the reactivity-/selectivity-determining step. Molecular-level models for these effects have far-reaching consequences in stereoselective ion pair catalysis.

Effect of carbon chain length on catalytic C–O bond cleavage of polyols over Rh-ReOx/ZrO2 in aqueous phase

Production of linear deoxygenated C4 (butanetriols, -diols, and butanols), C5 (pentanetetraols, -triols, -diols, and pentanols), and C6 products (hexanepentaols, -tetraols, -triols, -diols, and hexanols) is achievable by hydrogenolysis of erythritol, xylitol, and sorbitol over supported-bimetallic Rh-ReOx (Re/Rh molar ratio 0.5) catalyst, respectively. After validation of the analytical methodology, the effect of some reaction parameters was studied. In addition to C–O bond cleavage by hydrogenolysis, these polyols can undergo parallel reactions such as epimerization, cyclic dehydration, and C–C bond cleavage. The time courses of each family of linear deoxygenated C4, C5, and C6 products confirmed that the sequence of appearance of the different categories of deoxygenated products followed a multiple sequential deoxygenation pathway. The highest selectivity to a mixture of linear deoxygenated C4, C5, and C6 products at 80percent conversion was favoured under high pressure in the presence of 3.7wt.percentRh-3.5wt.percentReOx/ZrO2 catalysts (54–71percent under 80 bar) at 200 °C.

Controlling Sugar Deoxygenation Products from Biomass by Choice of Fluoroarylborane Catalyst

The feedstocks from biomass are defined and limited by nature, but through the choice of catalyst, one may change the deoxygenation outcome. We report divergent but selective deoxygenation of sugars with triethylsilane (TESH) and two fluoroarylborane catalysts, B(C6F5)3 and B(3,5-CF3)2C6H3)3 (BAr3,5-CF3). To illustrate, persilylated 2-deoxyglucose shows exocyclic C-O bond cleavage/reduction with the less sterically congested BAr3,5-CF3, whereas endocyclic C-O bond cleavage/reduction predominates with the more Lewis acidic B(C6F5)3. Chiral furans and linear polyols can be selectively synthesized depending on the catalysts. Mechanistic studies demonstrate that the resting states of these catalysts are different.

METHOD FOR PRODUCING L-FUCOSE

Method for producing L-fucose includes in a first aspect, a method for the preparation of L-fucose, wherein L-fucose precursors are produced from pectin and L-fucose is produced from the L-fucose precursors; in a second aspect, a method for the preparation of L-fucose from D-galacturonic acid or a salt thereof, wherein L-fucose precursors are produced from D-galacturonic acid of a salt thereof, and L-fucose is produced from the L-fucose precursors; and an L-fucose precursor as shown in Formula A, wherein R is a linear or branched chain saturated hydrocarbon group with 1-6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, etc., preferably a methyl group.

METHOD FOR PRODUCING L-FUCOSE

The present invention provides: in a first aspect, a method for the preparation of L-fucose, wherein L-fucose precursors are produced from pectin and L-fucose is produced from the L-fucose precursors; in a second aspect, a method for the preparation of L-fucose from D-galacturonic acid or a salt thereof, wherein L-fucose precursors are produced from D-galacturonic acid or a salt thereof, and L-fucose is produced from the L-fucose precursors; and an L-fucose precursoras shown in Formula A below, wherein R is a linear or branched chain saturated hydrocarbon group with 1-6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-hexyl, etc., preferably a methyl group.

DEOXYKETOHEXOSE ISOMERASE AND METHOD FOR PRODUCING DEOXYHEXOSE AND DERIVATIVE THEREOF USING SAME

Providing 1- or 6-deoxy products corresponding to all of aldohexoses, ketohexoses and sugar alcohols, as based on Deoxy-Izumoring, as well as a method for systematically producing those products. A method for producing deoxyketohexose and a derivative thereof using a deoxyketohexose isomerase derived from Pseudomonas cichorii ST-24 (FERM BP-2736), comprising epimerizing 1-deoxy D-ketohexose or 6-deoxy D-ketohexose or 1-deoxy L-ketohexose or 6-deoxy L-ketohexose at position 3 to produce the individually corresponding 1-deoxy D-ketohexose or 6-deoxy D-ketohexose or 1-deoxy L-ketohexose or 6-deoxy L-ketohexose as an intended product.