576-42-1

Usage

Uses

Used in Pharmaceutical Industry:
Potassium bisaccharate is used as an intermediate in the synthesis of D-Glucaro-1,4-lactone Monohydrate (G415600), which is an anticancer agent. This application takes advantage of its chemotherapeutic properties to contribute to the development of cancer treatments.
Used in Chelating Applications:
Potassium bisaccharate serves as a chelating agent, which is essential in various industrial processes. Its ability to form complexes with metal ions makes it useful in applications where metal ion sequestration is required.
Used in Rubber Formulations:
In the rubber industry, potassium bisaccharate is used to enhance the properties of rubber formulations. Its chelating properties can improve the stability and performance of rubber products.
Used in Metal Plating:
Potassium bisaccharate is utilized in metal plating processes due to its chelating capabilities. It helps in the efficient deposition of metals on various surfaces, improving the quality and durability of the plated products.
Used in Soap and Detergent Industry:
In the soap and detergent industry, potassium bisaccharate is used to improve the cleaning properties of these products. Its chelating action helps to remove dirt and stains more effectively, providing better cleaning results.

InChI:InChI=1/C6H10O8.K/c7-1(3(9)5(11)12)2(8)4(10)6(13)14;/h1-4,7-10H,(H,11,12)(H,13,14);/q;+1/p-1

Synthetic route

D-Glucose (2280-44-6) → D-glucaric acid monopotassium salt (576-42-1)

Conditions	Yield
With potassium hydroxide; chlorine; potassium bromide; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl In water at 0 - 5℃; pH=11.4 - 11.7; Product distribution; Further Variations:; Reagents;	77%

D-glucose (50-99-7) → C6H5O9(3-)*3K(1+) + C6H5O9(3-)*3K(1+) + D-glucaric acid monopotassium salt (576-42-1)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium D-gluconate; potassium hydroxide In water at 5℃; pH=12.2; Electrochemical reaction; optical yield given as %de;	A n/a B n/a C 70%

D-Glucuronic acid (6556-12-3) → D-glucaric acid monopotassium salt (576-42-1)

Conditions	Yield
With peracetic acid; potassium hydroxide; ethylenediaminetetraacetic acid; cyfluthrin; potassium hydrogencarbonate; potassium bromide In water

D-glucaric acid (87-73-0) → D-glucaric acid monopotassium salt (576-42-1)

Conditions	Yield
Stage #1: D-glucaric acid With potassium hydroxide In water Stage #2: With hydrogenchloride In water pH=3.4; Cooling with ice;	83.2 g

alpha-D-glucopyranose (492-62-6) → D-glucaric acid monopotassium salt (576-42-1)

Conditions	Yield
With oxygen; potassium hydroxide In water at 50℃; under 750.075 Torr; for 4h;
With platinum on activated charcoal; oxygen; potassium hydroxide at 50℃; under 750.075 Torr; for 4h; pH=4;

L-gulose (6027-89-0) → D-glucaric acid monopotassium salt (576-42-1)

Conditions	Yield
Stage #1: L-gulose With nitric acid; potassium hydroxide; sodium nitrite pH=Ca. 9 - Ca. 10; Stage #2: With nitric acid at 15 - 30℃; for 12h; pH=Ca. 3 - Ca. 4;

D-glucaric acid monopotassium salt (576-42-1) → D-glucaric acid (87-73-0) + D-Glucaro-1,4-lacton (389-36-6) + D-glucaro-6,3-lactone (2782-04-9)

Conditions	Yield
With H(1+) resin Rexyn 100(H) In water for 3h; lactonization;	A n/a B n/a C 69.1%

ethanol (64-17-5) + D-glucaric acid monopotassium salt (576-42-1) → diethyl glucarate (45214-05-9) + (S)-((2S,3R,4R)-3,4-Dihydroxy-5-oxo-tetrahydro-furan-2-yl)-hydroxy-acetic acid ethyl ester + D-glucarate-6,3-lactone ethyl ester (261900-70-3)

Conditions	Yield
With REXYN 101(H) at 55℃; for 4h;	A n/a B n/a C 58.9%

methanol (67-56-1) + D-glucaric acid monopotassium salt (576-42-1) → glucaric acid dimethyl ester (3868-17-5) + methyl D-glucarate 1,4-lactone (22140-16-5) + Methyl D-glucarate 6,3-lactone (155976-55-9)

Conditions	Yield
With hydrogenchloride for 4h; Heating;	A n/a B 58.89% C n/a
With hydrogenchloride for 4h; Heating;

[Cu4(μ-OH)(μ-α-D-glucose-1-phosphate(2-))2(2,2'-bipyridyl)4(H2O)2](NO3)3*10H2O + D-glucaric acid monopotassium salt (576-42-1) → [Cu4(μ-α-D-glucose-1-phosphate(2-))2(μ-D-glucaratoH)2(2,2'-bipyridyl)4](NO3)2*2H2O

Conditions	Yield
In water; N,N-dimethyl-formamide K glucarate (2 equiv.) in H2O added to soln. of Cu complex in DMF; stirred for 5 min; solvent removed under reduced pressure; crystd. from MeOH at room temp. for several d; crystals collected; washed with Et2O; dried under vac.; elem. anal.;	49%

[Cu4(μ-OH)(μ-α-D-glucose-1-phosphate(2-))2(2,2'-bipyridyl)4(H2O)2](NO3)3*10H2O + D-glucaric acid monopotassium salt (576-42-1) → ([Cu4(μ-α-D-glucose-1-phosphate(2-))2(μ-D-glucarateH)2(2,2'-bipyridyl)4](NO3)2*8H2O)(n)

Conditions	Yield
In N,N-dimethyl-formamide K glucarate (1 equiv.) added to soln. of Cu complex in DMF; stirred for 5 min; solvent removed under reduced pressure; crystd. from MeOH at room temp. for several d; crystals collected; washed with Et2O; dried under vac.; elem. anal.;	34%

D-glucaric acid monopotassium salt (576-42-1) + butan-1-ol (71-36-3) → glucaric acid di-n-butyl ester

Conditions	Yield
With Amberlyst-15 at 75℃; for 1.5h; Time;	25%

methanol (67-56-1) + D-glucaric acid monopotassium salt (576-42-1) → glucaric acid dimethyl ester (3868-17-5)

Conditions	Yield
With ion-exchange resin + form>

diethyl sulfate (64-67-5) + ethyl iodide (75-03-6) + D-glucaric acid monopotassium salt (576-42-1) → Tetraaethylzuckersaeure-diaethylester (109721-79-1)

Conditions	Yield
(i) aq. NaOH, (ii) /BRN= 1209714/, (iii) /BRN= 505934/, Ag2O; Multistep reaction;

D-glucaric acid monopotassium salt (576-42-1) + dimethyl sulfate (77-78-1) → tetramethyl-d-saccharic acid (14307-81-4)

Conditions	Yield
(i) aq. NaOH, (ii) /BRN= 635994/; Multistep reaction;

D-glucaric acid monopotassium salt (576-42-1) + dimethyl sulfate (77-78-1) + methyl iodide (74-88-4) → O2,O3,O4,O5-tetramethyl-D-glucaric acid dimethyl ester (102264-45-9)

Conditions	Yield
(i) aq. NaOH, (ii) /BRN= 635994/, (iii) /BRN= 969135/, Ag2O; Multistep reaction;

D-glucaric acid monopotassium salt (576-42-1) + methyl iodide (74-88-4) → O2,O3,O4,O5-tetramethyl-D-glucaric acid dimethyl ester (102264-45-9)

Conditions	Yield
(i) aq. NH3, AgNO3, (ii) /BRN= 969135/, DMF, (iii) /BRN= 969135/, Ag2O; Multistep reaction;

formaldehyd (50-00-0) + D-glucaric acid monopotassium salt (576-42-1) → 2,4:3,5-di-O-methylene-D-glucaric acid dimethyl ester (4539-77-9, 7595-91-7, 114006-01-8, 114421-41-9)

Conditions	Yield
With sulfuric acid	4.77 g

D-glucaric acid monopotassium salt (576-42-1) → (2R,3S,4S,5S)-5-(2-Amino-ethylcarbamoyl)-2,3,4,5-tetrahydroxy-pentanoic acid methyl ester; hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 91.7 percent / methanol / 3 h / 95 °C 3: acetyl chloride / 3 h / 20 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → (2R,3S,4S,5S)-5-(4-Amino-butylcarbamoyl)-2,3,4,5-tetrahydroxy-pentanoic acid methyl ester; hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 94.9 percent / methanol / 3 h / 95 °C 3: acetyl chloride / 3 h / 20 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → (2R,3S,4S,5S)-5-(6-Amino-hexylcarbamoyl)-2,3,4,5-tetrahydroxy-pentanoic acid methyl ester; hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 90.9 percent / methanol / 3 h / 95 °C 3: acetyl chloride / 3 h / 20 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → 6-[N-(2'-aminoethyl)]-D-glucaramide, sodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 91.7 percent / methanol / 3 h / 95 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → (2R,3S,4S,5S)-5-(8-Amino-octylcarbamoyl)-2,3,4,5-tetrahydroxy-pentanoic acid methyl ester; hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 93.8 percent / methanol / 3 h / 95 °C 3: acetyl chloride / 3 h / 20 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → 6-[N-(4'-aminobutyl)]-D-glucaramide, sodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 94.9 percent / methanol / 3 h / 95 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → (2R,3S,4S,5S)-5-(10-Amino-decylcarbamoyl)-2,3,4,5-tetrahydroxy-pentanoic acid methyl ester; hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 90.3 percent / methanol / 3 h / 95 °C 3: acetyl chloride / 3 h / 20 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → 6-[N-(6'-aminohexyl)]-D-glucaramide, sodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 90.9 percent / methanol / 3 h / 95 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → (2R,3S,4S,5S)-5-(12-Amino-dodecylcarbamoyl)-2,3,4,5-tetrahydroxy-pentanoic acid methyl ester; hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 91.5 percent / methanol / 3 h / 95 °C 3: acetyl chloride / 3 h / 20 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → 6-[N-(8'-aminooctyl)]-D-glucaramide, sodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 93.8 percent / methanol / 3 h / 95 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → 6-[N-(10'-aminodecyl)]-D-glucaramide, sodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 90.3 percent / methanol / 3 h / 95 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → 6-[N-(12'-aminododecyl)]-D-glucaramide, sodium salt

Conditions	Yield
Multi-step reaction with 2 steps 1: 69.1 percent / H(1+) resin Rexyn 100(H) / H2O / 3 h 2: 91.5 percent / methanol / 3 h / 95 °C View Scheme

D-glucaric acid monopotassium salt (576-42-1) → N,N'-dimethyl-D-glucaramide (156016-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / 4 h / Heating 2: 90.9 percent / methanol; H2O / 2 h / Ambient temperature View Scheme

D-glucaric acid monopotassium salt (576-42-1) → Dimethyl 2,3,4,5-tetrakis-O--D-glucarate

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / 4 h / Heating 2: 1.) acetyl chloride, 2.) 1,1,1,3,3,3-hexamethyldisilazane, pyridine / 1.) MeOH, reflux, 12 h, 2.) r.t., 2 d View Scheme

D-glucaric acid monopotassium salt (576-42-1) → Methyl 2,4,5-tris-O--D-glucarate 6,3-lactone

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / 4 h / Heating 2: 1.) acetyl chloride, 2.) 1,1,1,3,3,3-hexamethyldisilazane, pyridine / 1.) MeOH, reflux, 12 h, 2.) r.t., 2 d View Scheme

D-glucaric acid monopotassium salt (576-42-1) → Methyl 2,3,5-tris-O--D-glucarate 1,4-lactone

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / 4 h / Heating 2: 1.) acetyl chloride, 2.) 1,1,1,3,3,3-hexamethyldisilazane, pyridine / 1.) MeOH, reflux, 12 h, 2.) r.t., 2 d View Scheme
Multi-step reaction with 2 steps 1: HCl / 4 h / Heating 2: 1,1,1,3,3,3-hexamethyldisilazane, pyridine / methanol / Ambient temperature View Scheme

Upstream product

• 50-99-7 D-glucose 
• 87-73-0 D-glucaric acid 
• 2280-44-6 D-Glucose 
• 5978-95-0 D-idose 
• 5934-56-5 glucose 
• 492-62-6 alpha-D-glucopyranose 
• 6556-12-3 D-Glucuronic acid 
• 576-42-1 D-saccharic acid potassium salt 
• 6027-89-0 L-gulose 

Downstream Products

• 122990-47-0 catena{D-saccharatetriaquamagnesium} 
• 6614-50-2 D-glucaramide 
• 627-93-0 hexanedioic acid dimethyl ester 
• 87-73-0 D-glucaric acid 
• 389-36-6 D-Glucaro-1,4-lacton 
• 2782-04-9 D-glucaro-6,3-lactone 
• 105-99-7 adipic acid dibutyl ester 
• 826-91-5 D-glucaric acid 1,4:6,3-dilactone 
• 4539-77-9 2,4:3,5-di-O-methylene-D-glucaric acid dimethyl ester 
• 3238-40-2 furan-2,5-dicarboxylic acid 

Relevant academic research and scientific papers

Modifications in the nitric acid oxidation of d-glucose

The nitric acid oxidation of d-glucose was reinvestigated in an effort to better understand and improve the oxidation and subsequent work up steps. The oxidation was carried out using a computer controlled reactor employing a closed reaction flask under an atmosphere of oxygen which allowed for a catalytic oxidation process with oxygen as the terminal oxidant. Removal of nitric acid from product included the use of both diffusion dialysis and nanofiltration methodologies. Product analysis protocols were developed using ion chromatography.

Evidence of benzilic rearrangement during the electrochemical oxidation of D-glucose to D-glucaric acid

During the course of the 2,2,6,6-tetramethyl-1-piperidinyloxy free radical-catalyzed electrochemical oxidation of d-glucose to d-glucaric acid a new side-product was observed. This compound was isolated and identified as a tricarboxylic acid of unique structure, which was named maribersonic acid. Its structure was proven by different experiments coupled with several analytical methods, and its appearance during the electrochemical oxidation of d-glucose was rationalized through a thorough study.

METHOD FOR PRODUCING ADIPAMIDE AS INTERMEDIATE FOR PRODUCTION OF RAW MATERIAL FOR BIO-BASED NYLON

Disclosed is a method for producing adipamide, which may include the steps of: (a) reacting glucose, nitric acid (HNO3), sodium nitrite (NaNO2) and potassium hydroxide (KOH) to produce a glucaric acidpotassium salt, (b) producing glucamide by reacting the glutaric acid potassium salt, with an acidic solution and removing a potassium ion from the glucaric acid potassium salt, (c) preparing an reaction admixture by adding the glucamide and a catalyst to hydrogen halide and acetic acid, and (d) treating the reaction admixture with hydrogen gas in a reactor thereby producing the adipamide.

METHOD OF PREPARING D-GLUCARO-1,4:6,3-DILACTONE

Disclosed is a method of preparing d-glucaro-1,4:6,3-dilactone using an organic acid or a salt thereof, such that d-glucaro-1,4:6,3-dilactone having high purity can be obtained using potassium glucarate as the organic acid, and simultaneously, the economic efficiency of the preparation process can be remarkably improved.

METHOD OF PREPARING ADIPIC ACID

Disclosed is a method of preparing adipic acid from d-glucaro-1,4:6,3-dilactone, particularly using a rhenium catalyst and a noble metal catalyst. Further the method may include using an environmentally friendly solvent such as water. Thus, the obtained adipic acid may have high purity as a final product and economic efficiency of the preparation process may be improved.

METHOD FOR PRODUCING ADIPAMIDE AS INTERMEDIATE FOR PRODUCTION OF RAW MATERIAL FOR BIO-BASED NYLON

Disclosed is a method for producing adipamide, which may include the steps of: (a) reacting glucose, nitric acid (HNO3), sodium nitrite (NaNO2) and potassium hydroxide (KOH) to produce a glucaric acid potassium salt, (b) producing glucamide by reacting the glutaric acid potassium salt, with an acidic solution and removing a potassium ion from the glucaric acid potassium salt, (c) preparing an reaction admixture by adding the glucamide and a catalyst to hydrogen halide and acetic acid, and (d) treating the reaction admixture with hydrogen gas in a reactor thereby producing the adipamide.

Method of oxidization using nitric acid

A controlled nitric acid process employing oxygen and nitric acid as co-oxidants is used to oxidize organic compounds subject to nitric acid oxidation, to their corresponding carboxylic acids. Oxidation of some carbohydrates by this process can produce one or more of their corresponding acid forms. The process is carried out at moderate temperatures, typically in the range of 20° C. to 45° C. in a closed reactor, with oxygen gas being introduced into the reaction chamber as needed in order to sustain the reaction. Computer controlled reactors allow for careful and reproducible control of reaction parameters. Nitric acid can be recovered by a distillation/evaporation process, or by diffusion dialysis, the aqueous solution made basic with inorganic hydroxide, and the residual inorganic nitrate removed using a filtration (nanofiltration) device. The method eliminates issues of thermal control of the oxidation, release of nitrogen into the atmosphere, and post-reaction difficulties in the removal of nitric acid and inorganic nitrates.

Process for selective oxidation of primary alcohols

Primary alcohols, especially in carbohydrates, can be selectively oxidized to aldehydes and carboxylic acids in a low-halogen process by using a peracid in the presence of a catalytic amount of a di-tertiary-alkyl nitroxyl (TEMPO) and a catalytic amount of halide. The halide is preferably bromide and the process can be carried out at nearly neutral to moderately alkaline pH (5-11). The peracid can be produced or regenerated by means of hydrogen peroxide or oxygen. The process is advantageous for producing uronic acids and for introducing aldehyde groups which are suitable for crosslinking and derivatization.

4-AcNH-Tempo-catalyzed oxidation of aldoses to aldaric acids using chlorine or bromine as terminal oxidants

The 4-AcNH-TEMPO-catalyzed oxidation of D-glucose to D-glucaric acid using elemental chlorine or bromine as the terminal oxidant is reported. The pH and temperature of the reactions were closely controlled to be between 0-5 deg C and pH 11.5, respectively. Spectroscopically (1H NMR) determined yields of glucarate were greater than 90 percent; yields of crystalline monopotassium D-glucarate (or disodium D-glucarate), isolated and purified by precipitation, were between 70 and 85 percent. Oxidations of mannose to mannaric acid and galactose to mucic acid were also demonstrated.

Facile nitroxide-mediated oxidations of D-glucose to D-glucaric acid

The oxidation of D-(+)-glucose to D-glucaric acid using the TEMPO-like nitroxide oxidation catalyst, 4-acetamido-2,2,6,6-tetramethyl-1-piperidinyloxy (4-acetamido-TEMPO) was carried out using several oxidizing agents and co-catalyst. The pH and temperature of the reactions were closely monitored to decrease degradations during the oxidation, and several isolation methods were explored.