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66357-35-5

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66357-35-5 Usage

Description

Ranitidine, a H2-receptor agonist, caused contact dermatitis within the pharmaceutical industry.

Uses

Different sources of media describe the Uses of 66357-35-5 differently. You can refer to the following data:
1. Antagonist (to histamine H2receptors).
2. It simultaneously reduces pepsin activity and is used for treating stomach and duodenum ulcers as well as other conditions accompanied by elevated acidity of the gastrointestinal tract. Synonyms of this drug are zantac, azantac, raniplex, ranidil, and others.
3. Ranitidine (cas# 66357-35-5) was used as a standard for testing the therapeutic effect of brown propolis extract against aspirin and ethanol- induced gastric ulcers.

Indications

Ranitidine (Zantac) is another H2 receptor antagonist that does not have the same antiandrogen side effects as cimetidine. Note that both cimetidine and ranitidine inhibit the cytochrome P-450 microsomal enzyme system.

General Description

Ranitidine, N-[2-[[[5-(dimethylamino)methyl]-2-furanyl]methyl]thiol] ethyl]-N'-methyl-2-nitro-l,1-ethenediamine (Zantac), is a white solid, which inits hydrochloride salt form is highly soluble in water. It is anaminoalkyl furan derivative with pKa values of 2.7 (sidechain) and 8.2 (dimethylamino). Ranitidine is more potentthan cimetidine, but less potent than famotidine. Likeother H2-antagonists, it does not appear to bind to otherreceptors.Bioavailability of an oral dose of ranitidine is about 50%and is not significantly affected by the presence of food.Some antacids may reduce ranitidine absorption and shouldnot be taken within 1 hour of administration of this drug. Theplasma half-life of the drug is 2 to 3 hours, and it is excretedalong with its metabolites in the urine. Three metabolites, ranitidineN-oxide, ranitidine S-oxide, and desmethyl ranitidine,have been identified. Ranitidine is only a weak inhibitor ofthe hepatic cytochrome isozymes, and recommended doses ofthe drug do not appear to inhibit the metabolism of otherdrugs. However, there have been isolated reports of drug interactions(warfarin, triazolam) that suggest that ranitidinemay affect the bioavailability of certain drugs by someunidentified mechanism, perhaps by pH-dependent effect onabsorption or a change in volume of distribution.In addition to being available in various dosage forms asthe hydrochloride salt, ranitidine is also available as a bismuthcitrate salt for use with the macrolide antibiotic clarithromycinin treating patients with an active duodenalulcer associated with H. pylori infection. Eradication of H.pylori reduces the risk of duodenal ulcer recurrence.

Biological Activity

Potent, selective and competitive histamine H 2 receptor antagonist (pA 2 = 6.95-7.2). In vivo, inhibits gastric acid secretion induced by histamine, pentagastrin, bethanecol and food. Also inhibits aspirin-induced gastric lesions.

Clinical Use

H2 antagonist: Conditions associated with hyperacidity

Synthesis

Ranitidine, N[2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl]- N′-methyl-2-nitro-1,1-ethendiamine (16.2.8), is synthesized from furfuryl alcohol, which undergoes aminomethylation reaction using dimethylamine and paraform, which form 5- (dimethylaminomethyl)furfuryl alcohol (16.2.6). Further reaction with 2-mercaptoethylamine hydrochloride gives a product of substitution of the hydroxyl group in (16.2.6), 5-dimethylaminomethyl-2-(2′-aminoethyl)thiomethylfurane (16.2.7). Reacting this with Nmethyl- 1-methylthio-2-nitroethenaamine gives ranitidine (16.2.8).

Drug interactions

Potentially hazardous interactions with other drugs Alpha-blockers: effects of tolazoline antagonised. Antifungals: absorption of itraconazole and ketoconazole reduced; concentration of posaconazole possibly reduced - avoid. Antivirals: concentration of atazanavir reduced; concentration of raltegravir possibly increased - avoid; avoid for 12 hours before and 4 hours after rilpivirine. Ciclosporin: may increase or not change ciclosporin levels; nephrotoxicity, additive hepatotoxicity and thrombocytopenia reported. Cytotoxics: reduced gefitinib concentration; reduces concentration of erlotinib and possibly pazopanib, give at least 2 hours before or 10 hours after ranitidine; absorption of dasatinib reduced - avoid; possibly reduced absorption of lapatinib. Ulipristal: contraceptive effect possibly reduced - avoid with high dose ulipristal.

Metabolism

Ranitidine is not extensively metabolised. A small proportion of ranitidine is metabolised in the liver to the N-oxide, the S-oxide, and desmethylranitidine; the N-oxide is the major metabolite but accounts for only about 4-6% of a dose. The fraction of the dose recovered as metabolites is similar after both oral and IV dosing; and includes 6% of the dose in urine as the N-oxide, 2% as the S-oxide, 2% as desmethylranitidine and 1-2% as the furoic acid analogue. There is also some excretion in the faeces.

Dosage forms

150 mg b.i.d.

Check Digit Verification of cas no

The CAS Registry Mumber 66357-35-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,3,5 and 7 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 66357-35:
(7*6)+(6*6)+(5*3)+(4*5)+(3*7)+(2*3)+(1*5)=145
145 % 10 = 5
So 66357-35-5 is a valid CAS Registry Number.
InChI:InChI=1/C13H22N4O3S/c1-14-13(9-17(18)19)15-6-7-21-10-12-5-4-11(20-12)8-16(2)3/h4-5,9,14-15H,6-8,10H2,1-3H3/b13-9+

66357-35-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name ranitidine

1.2 Other means of identification

Product number -
Other names Taural

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:66357-35-5 SDS

66357-35-5Synthetic route

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine
61832-41-5

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
66356-53-4

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
In water at 55℃;92%
1,1-dichloro-2-nitro ethylene
6061-04-7

1,1-dichloro-2-nitro ethylene

2-mercaptoethylamine hydrochloride
156-57-0

2-mercaptoethylamine hydrochloride

5-(N,N'-dimethylaminomethyl)-2-chloromethyl-furan

5-(N,N'-dimethylaminomethyl)-2-chloromethyl-furan

methylamine
74-89-5

methylamine

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
Stage #1: 1,1-dichloro-2-nitro ethylene; 2-mercaptoethylamine hydrochloride With sodium hydroxide at 50℃; for 1h;
Stage #2: methylamine With calcium oxide In ethanol at 20℃; for 12h;
Stage #3: 5-(N,N'-dimethylaminomethyl)-2-chloromethyl-furan In ethanol; water at 45℃; for 2h; Temperature;
90%
(Z)-1-β-hydroxyethylamino-1-methylamino-2-nitroethene

(Z)-1-β-hydroxyethylamino-1-methylamino-2-nitroethene

5-(N,N-dimethylaminomethyl)-2-thiomethylfuran hydrobromide

5-(N,N-dimethylaminomethyl)-2-thiomethylfuran hydrobromide

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
Stage #1: (Z)-1-β-hydroxyethylamino-1-methylamino-2-nitroethene; 5-(N,N-dimethylaminomethyl)-2-thiomethylfuran hydrobromide With hydrogenchloride at 0℃; for 40h;
Stage #2: With sodium hydroxide; sodium chloride at 0℃; pH=9;
17.3%
nitromethane
75-52-5

nitromethane

N-methyl-N'-(2-<(5-dimethylaminomethyl)-furan-2-ylmethylthio>-ethyl)-carbodiimide
91756-97-7

N-methyl-N'-(2-<(5-dimethylaminomethyl)-furan-2-ylmethylthio>-ethyl)-carbodiimide

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
With sodium hydride 1.) DMF, 30 min, room temp., 2.) DMF, 90 min; Yield given. Multistep reaction;
N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

5-[2-((E)-1-Methylamino-2-nitro-vinylamino)-ethylsulfanylmethyl]-furan-2-carbaldehyde

5-[2-((E)-1-Methylamino-2-nitro-vinylamino)-ethylsulfanylmethyl]-furan-2-carbaldehyde

A

Ranitidine
66357-35-5

Ranitidine

B

N-[2-[[[5-(hydroxymethyl)-2-furanyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine

N-[2-[[[5-(hydroxymethyl)-2-furanyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine

Conditions
ConditionsYield
With sodium acetate; sodium cyanoborohydride In methanol 1) -70 deg C, 3 h, 2) -18 deg C; Yield given;
N-methyl-N'-(2-<(5-dimethylaminomethyl)-furan-2-ylmethylthio>-ethyl)-urea
66357-07-1

N-methyl-N'-(2-<(5-dimethylaminomethyl)-furan-2-ylmethylthio>-ethyl)-urea

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 52 percent / (C6H5)3PBr2, (C2H5)3N / CH2Cl2 / 2 h
2: 1.) NaH / 1.) DMF, 30 min, room temp., 2.) DMF, 90 min
View Scheme
2-(nitromethylene)thiazolidine
94662-61-0

2-(nitromethylene)thiazolidine

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

5-chloromethyl-2-furfuryldimethylamine hydrochloride

5-chloromethyl-2-furfuryldimethylamine hydrochloride

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
With methylamine In acetonitrile
2-(nitromethylene)thiazolidine
94662-61-0

2-(nitromethylene)thiazolidine

5-chloromethyl-2-furfuryldimethylamine hydrochloride

5-chloromethyl-2-furfuryldimethylamine hydrochloride

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
With sodium hydroxide; methylamine In water; isopropyl alcohol
With sodium acetate; potassium carbonate; methylamine In 4-methyl-2-pentanone; acetonitrile
N-[2-[[5-(1,3-dioxolan-2-yl)-2-furanylmethyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine

N-[2-[[5-(1,3-dioxolan-2-yl)-2-furanylmethyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

pyrographite
7440-44-0

pyrographite

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
With hydrogenchloride; ammonia; sodium cyanoborohydride; sodium carbonate; acetic acid; dimethyl amine In tetrahydrofuran; methanol; ethanol; water
N-(2-chloroethyl)-N'-methyl-2-nitro-1,1-ethenediamine

N-(2-chloroethyl)-N'-methyl-2-nitro-1,1-ethenediamine

5-[(Dimethylamino)methyl]-2-furanmethanethiol, oxalate

5-[(Dimethylamino)methyl]-2-furanmethanethiol, oxalate

pyrographite
7440-44-0

pyrographite

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; ethanol; water
1,4-dioxane
123-91-1

1,4-dioxane

methanol-0.88 ammonia

methanol-0.88 ammonia

N-[2-[[5-(1,3-dioxolan-2-yl)-2-furanylmethyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine

N-[2-[[5-(1,3-dioxolan-2-yl)-2-furanylmethyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
With hydrogenchloride; sodium cyanoborohydride; sodium carbonate; acetic acid; dimethyl amine In tetrahydrofuran; water; 4-methyl-2-pentanone; acetone
N-[2-[[5-(1,3-dioxolan-2-yl)-2-furanylmethyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine

N-[2-[[5-(1,3-dioxolan-2-yl)-2-furanylmethyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
With hydrogenchloride; sodium borohydrid; sodium carbonate; dimethyl amine In tetrahydrofuran; ethanol; water
With hydrogenchloride; ammonia; sodium cyanoborohydride; sodium carbonate; dimethyl amine In tetrahydrofuran; ethanol; dichloromethane; Isopropyl acetate; water; acetic acid
(5-dimethylaminomethyl-furan-2-yl)-methanol
15433-79-1

(5-dimethylaminomethyl-furan-2-yl)-methanol

methanol-0.88 ammonia

methanol-0.88 ammonia

N,N'-bis-[Thio(2,1-ethanediyl)]bis(N'-methyl-2-nitro-1,1-ethenediamine)

N,N'-bis-[Thio(2,1-ethanediyl)]bis(N'-methyl-2-nitro-1,1-ethenediamine)

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran; hydrogenchloride
ethyleneimine
151-56-4

ethyleneimine

1-[[5-[(dimethylamino)methyl]-2-furanylmethyl]thio]-N-methyl-2-nitroethenamine

1-[[5-[(dimethylamino)methyl]-2-furanylmethyl]thio]-N-methyl-2-nitroethenamine

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
In water; 4-methyl-2-pentanone
N-[2-[[5-(1,3-dioxolan-2-yl)-2-furanylmethyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine

N-[2-[[5-(1,3-dioxolan-2-yl)-2-furanylmethyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
With hydrogenchloride; sodium borohydrid; ammonia; acetic acid; dimethyl amine In tetrahydrofuran; ethanol
N-(2-chloroethyl)-N'-methyl-2-nitro-1,1-ethenediamine

N-(2-chloroethyl)-N'-methyl-2-nitro-1,1-ethenediamine

1-[[[5-[(Dimethylamino)methyl]-2-furanyl]methyl]thio]methanimidamide, maleate

1-[[[5-[(Dimethylamino)methyl]-2-furanyl]methyl]thio]methanimidamide, maleate

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; water; magnesium sulfate
With potassium hydroxide; sodium carbonate In tetrahydrofuran; water
N-(2-chloroethyl)-N'-methyl-2-nitro-1,1-ethenediamine

N-(2-chloroethyl)-N'-methyl-2-nitro-1,1-ethenediamine

5-[(Dimethylamino)methyl]-2-furanmethanethiol, oxalate

5-[(Dimethylamino)methyl]-2-furanmethanethiol, oxalate

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; water; 4-methyl-2-pentanone
5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine
66356-53-4

5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine

pyrographite
7440-44-0

pyrographite

1,1-di(methylsulfanyl)-2-nitroethylene
13623-94-4

1,1-di(methylsulfanyl)-2-nitroethylene

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
In methanol; methanolic methylamine; acetonitrile
(5-dimethylaminomethyl-furan-2-yl)-methanol
15433-79-1

(5-dimethylaminomethyl-furan-2-yl)-methanol

N-(2-mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine

N-(2-mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
In hydrogenchloride
(furan-2-ylmethyl)dimethylamine
14496-34-5

(furan-2-ylmethyl)dimethylamine

N-(2-mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine

N-(2-mercaptoethyl)-N'-methyl-2-nitro-1,1-ethenediamine

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
With paraformaldehyde In hydrogenchloride; acetic acid
5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogenchloride / dichloromethane / 20 °C
2.1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: methanol / 0.67 h / 20 °C
3.2: 0.33 h / 0 °C
4.1: water / 2.5 h / Reflux; Alkaline conditions
5.1: water / 55 °C
View Scheme
5-chloromethylfurfural
1623-88-7

5-chloromethylfurfural

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere
1.2: 20 °C / Inert atmosphere
2.1: methanol / 0.67 h / 20 °C
2.2: 0.33 h / 0 °C
3.1: water / 2.5 h / Reflux; Alkaline conditions
4.1: water / 55 °C
View Scheme
5-[[(2-acetamidoethyl)thio]methyl]furfural
1350914-20-3

5-[[(2-acetamidoethyl)thio]methyl]furfural

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanol / 0.67 h / 20 °C
1.2: 0.33 h / 0 °C
2.1: water / 2.5 h / Reflux; Alkaline conditions
3.1: water / 55 °C
View Scheme
5-[[(2-acetamidoethyl)thio]methyl]-N,N-dimethyl-2-furanmethanamine
79589-16-5

5-[[(2-acetamidoethyl)thio]methyl]-N,N-dimethyl-2-furanmethanamine

Ranitidine
66357-35-5

Ranitidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water / 2.5 h / Reflux; Alkaline conditions
2: water / 55 °C
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 1-butyl-3-methylimidazolium chloride; sulfuric acid / 60 °C
2.1: hydrogenchloride / dichloromethane / 20 °C
3.1: sodium hydride / tetrahydrofuran / 0.5 h / Inert atmosphere
3.2: 20 °C / Inert atmosphere
4.1: methanol / 0.67 h / 20 °C
4.2: 0.33 h / 0 °C
5.1: water / 2.5 h / Reflux; Alkaline conditions
6.1: water / 55 °C
View Scheme
Ranitidine
66357-35-5

Ranitidine

ranitidine hydrochloride
66357-59-3, 71130-06-8

ranitidine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 0℃; pH=4.5 - 6.5; Temperature; pH-value;93.84%
With hydrogenchloride for 2.03333h;
Ranitidine
66357-35-5

Ranitidine

atorvastatin
134523-00-5

atorvastatin

atorvastatin; ranitidine salt

atorvastatin; ranitidine salt

Conditions
ConditionsYield
In ethyl acetate Product distribution / selectivity;
In methanol; 2-methylpropyl acetate Product distribution / selectivity;
ibuprofen
15687-27-1

ibuprofen

Ranitidine
66357-35-5

Ranitidine

ranitidinium ibuprofenate

ranitidinium ibuprofenate

Conditions
ConditionsYield
In acetone at 25℃; for 24h;

66357-35-5Relevant articles and documents

An improved synthesis of the antiulcer drug ranitidine from N-[2-[[[5- (hydroxymethyl)-2-furanyl]-methyl]-thio]-ethyl]-N'-methyl-2-nitro-1,1- ethenediamine

Aasen, Arne Jorgen,Skramstad, Jan

, p. 228 - 229 (1998)

An improved synthesis of the antiulcer drug ranitidine from N-[2-[[[5- (hydroxymethyl)-2-furanyl]-methyl]-thiol]-ethyl]-N'methyl-2-nitro-1,1- ethenediamine is reported.

New method for synthesizing ranitidine

-

Paragraph 0034; 0039-0044; 0047; 0052-0057; 0059; 0064-0069, (2018/12/14)

The invention discloses a new method for synthesizing ranitidine. The method comprises the steps of synthesizing vinylidene chloride, synthesizing 1, 1-dichloro-2-nitroethylene, carrying out a ring-closing reaction, carrying out a ring-opening reaction in presence of a desiccant, and synthesizing the ranitidine. The method adopts an anhydrous environment in the preparation process of a ring-opening product, thus avoiding the interference with the reaction and the generation of impurities due to the presence of water, reducing the post-treatment work and increasing the utilization rate of the raw materials. The preparation method provided by the invention effectively increases the reaction yield of the ring-opening product, improves the purity of the ring-opening reaction, and reduces the reaction time; therefore, the yield and purity of the product ranitidine are improved, the production cost is lowered, and the method is more beneficial to industrial production.

Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis

Galkin, Konstantin I.,Krivodaeva, Elena A.,Romashov, Leonid V.,Zalesskiy, Sergey S.,Kachala, Vadim V.,Burykina, Julia V.,Ananikov, Valentine P.

, p. 8338 - 8342 (2016/07/19)

Spectral studies revealed the presence of a specific arrangement of 5-hydroxymethylfurfural (5-HMF) molecules in solution as a result of a hydrogen–bonding network, and this arrangement readily facilitates the aging of 5-HMF. Deterioration of the quality of this platform chemical limits its practical applications, especially in synthesis/pharma areas. The model drug Ranitidine (Zantac) was synthesized with only 15 % yield starting from 5-HMF which was isolated and stored as an oil after a biomass conversion process. In contrast, a much higher yield of 65 % was obtained by using 5-HMF isolated in crystalline state from an optimized biomass conversion process. The molecular mechanisms responsible for 5-HMF decomposition in solution were established by NMR and ESI-MS studies. A highly selective synthesis of a 5-HMF derivative from glucose was achieved using a protecting group at O(6) position.

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