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3416-24-8

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3416-24-8 Usage

Outline

Glucosamine, also known as 2deoxy aminosamidose, is a common amino sugar and is a derivative of glucose. It is a compound formed by the substitution of hydroxyl on the second carbon atom of glucose molecule. A hydrogen atom on the amino group is often substituted by acetyl group to form N-acetylglucosamine. It rarely exists in organisms, mainly as chitin, glycoprotein and proteoglycan components.

Physicochemical properties

Its molecular formula is C6H13NO5, and its molecular weight is 179.17. Glucosamine has the property of polyhydroxylamines and exists in the cell walls of crustaceans, insects, molds and bacteria in the form of polymers or derivatives. Chitin (Nacetyl glucosamine condensate) produces amino glucosamine in water. The alpha body is crystalline and its melting point is 88 degrees, and it changes []D20100] to 47.5 degrees (30 minutes) in aqueous solution. The beta body can be obtained from methanol by acicular crystals, decomposing at 110 degrees, and changing in aqueous solution [alpha]D2028 degrees to 47.5 degrees (30 minutes). It is soluble in water, soluble in hot methanol, slightly soluble in cold methanol and ethanol, and insoluble in ethyl ether and chloroform. It exists in crustacean, mucin and mucin. It is a trace organic component in seawater, particulates and marine sediments. The content of marine samples can be separated by hydrolysis and cation exchange column and determined by spectrophotometry. Preparative method:dehydrated glucose and ammonia react in absolute ethanol, and then hydrolyze to produce crude glucosamine.

Natural Substance

Glucosamine hydrochloride is a natural substance that stimulates the body to make glycosaminoglycans to repair and form cartilage. Hydrochloride is a kind of easily absorbed small component, composed of amino acids such as glucose and glutamine. Its function is to stimulate the production of synovial fluid and promote articular cartilage repair. It also strengthens the synthesis of connective tissue. Hydrochloride is a hydrophilic molecule that absorbs water into cartilage and improves cartilage elasticity. Glucosamine is an amino acid naturally occurring in the human body. Its role is to form and repair cartilage. Although glucosamine is a natural substance produced by human body, its level decreases with aging, resulting in cartilage degeneration. Taking glucosamine as a nutritional supplement is one of the ways to help reduce the level of glucosamine in the body. Glucosamine nutritional supplement is the shell of crustacean seafood extracted from crabs, lobsters and shrimps. Crustacean seafood, like humans, naturally produces this substance. It is known that glucosamine nutritional supplements are effective for osteoarthritis. This is because glucosamine is the precursor of glycosaminoglycan, and the latter is the basic material for articular cartilage to repair cartilage tissue. The human body needs these glycosaminoglycans to make proteoglycans. Proteoglycan is a substance similar to clay made from protein and sugar. Before collagen is deposited in the joint, it is the basic material for cartilage. The more glycosaminoglycan in articular cartilage, the higher the rate of cartilage formation. As glucosamine is the precursor of glycosaminoglycan, glucosamine supplements help to reduce inflammation and swelling of the joints and rebuild damaged cartilage, which is beneficial to the treatment of osteoarthritis. Previous studies have shown that patients with mild to moderate osteoarthritis can feel pain relieved after taking glucosamine. Its analgesic effect is similar to aspirin and Bloven (Ibuprofen) and other non steroidal anti-inflammatory drugs (NSAIDs). Other studies have shown that glucosamine may help slow down cartilage damage in osteoarthritis patients.

Application

It is widely used in the fields of health medicine, health food, cosmetics and other fields. It plays an important role in improving the life rate of human activities and promoting the growth of human synthetic life substance.

Chemical Properties

(β form.) Colorless needles. Mp 110C (decomposes). Very soluble in water; slightly soluble in methanol and ethanol; insoluble in ether and chloroform.

Occurrence

Glucosamine is found in mucopolysaccharides, chitin, and mucoproteins. Glucosamine is a naturally occurring substance; glucosamine sulfate is manufactured synthetically.

Uses

Different sources of media describe the Uses of 3416-24-8 differently. You can refer to the following data:
1. Glucosamine is an amino sugar that can regulate growth factor gene transcription. It is also widely touted as remedy for osteoarthritis (OA).
2. Pharmaceutic aid.

Definition

ChEBI: The open-chain form of D-glucosamine.

Brand name

Adaxil;Antatril;Arthryl;Chitosamine;Corti-anartril;Dona 200-s;Dona compositum;Donna 200;Pona;Terramycin;Terrastatom;Tetracyn;Thiocondramine;Viartril.

World Health Organization (WHO)

Glucosamine is found in chitin, mucoproteins and mucopolysaccharides. It is used as a pharmaceutical aid. Glucosamine sulfate has been used in the treatment of rheumatic disorders though it is not widely marketed for this purpose.

Veterinary Drugs and Treatments

These compounds may be useful in treating osteoarthritis or other painful conditions in domestic animals, but large, well-designed controlled clinical studies proving efficacy were not located. One study in dogs (McCarthy, O’Donovan et al. 2007) showed some positive effect, but this study was not placebo controlled and compared responses versus carprofen. Another placebo-controlled, blinded study in dogs (Moreau, Dupuis et al. 2003), did not demonstrate statistically significant improvement after 60 days of treatment. These compounds potentially could be of benefit in cats with FLUTD (feline lower urinary tract disease) because of the presence of glycosaminoglycans as part of the protective layer of the urinary tract. Controlled studies have shown some positive effects in some cats, but overall did not appear to make a significant difference.

Purification Methods

Crystallise the amines from MeOH. The free base has been obtained from the hydrochloride (21.5g, see below) in a mixture of Et3N (15mL) and EtOH (125mL) by shaking for 2days at room temperature, and the solid Et3N.HCl is filtered off and the process repeated with more Et3N (3-4 times) until the D-glucosamine (15g) is free from Cl ions. It has m 88o , [] D20 +100o mutarotating to +47.5o (c 1, H2O). When Et2NH is used as base, the  to  conversion is complete giving D-glucosamine. The pentaacetate is purified by dissolving in CHCl3, treating with charcoal, drying (MgSO4), evaporating the solvent, and adding a little dry Et2O to induce crystallisation. It has m 124-126o, [] D +113o (c 1, CHCl3) after 16hours in a desiccator. [Leaback Biochemical Preparations 10 118 1963.] The N-acetyl derivative, m 203-205o from MeOH/Et2O (dry in vacuum P2O5) has [] D +75o to +41o (c 2, H2O); this derivative can also be purified by dissolving in the minimum volume of H2O to which is added 7-8volumes of EtOH followed by Et2O until turbid and keeping at ~20o to crystallise. Wash the crystals with MeOH then Et2O and dry in vacuo over P2O5. [Horton Biochemical Preparations 11 1 1966.]

Check Digit Verification of cas no

The CAS Registry Mumber 3416-24-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,4,1 and 6 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 3416-24:
(6*3)+(5*4)+(4*1)+(3*6)+(2*2)+(1*4)=68
68 % 10 = 8
So 3416-24-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H13NO5.ClH/c7-3-5(10)4(9)2(1-8)12-6(3)11;/h2-6,8-11H,1,7H2;1H/t2-,3-,4-,5-,6-;/m1./s1

3416-24-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name Glucosamine

1.2 Other means of identification

Product number -
Other names SYNTHETICGLUCOSAMINE

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:3416-24-8 SDS

3416-24-8Synthetic route

D-(+)-glucosamine hydrochloride
66-84-2

D-(+)-glucosamine hydrochloride

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol for 3h;99%
With triethylamine In methanol; water
chitosan (deacetylation degree, 93%)

chitosan (deacetylation degree, 93%)

sodium acetate
127-09-3

sodium acetate

A

chitosan oligosaccharides

chitosan oligosaccharides

B

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

C

2-acetamido-2-deoxy-D-glucose
7512-17-6

2-acetamido-2-deoxy-D-glucose

D

Low molecular weight chitosan

Low molecular weight chitosan

Conditions
ConditionsYield
With chitosanase In water at 40℃; for 20h; pH=4.5; Product distribution; Further Variations:; Reagents; pH-values; Enzymatic reaction;A 46.3%
B n/a
C n/a
D 44.6%
methanol
67-56-1

methanol

D-fructose-imine

D-fructose-imine

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
Behandeln mit Carbonsaeuren;
D-Fructose
57-48-7

D-Fructose

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With ammonia
With ammonium chloride; ammonia
methyl 2-amino-2-deoxy-β-D-glucopyranoside
3867-92-3

methyl 2-amino-2-deoxy-β-D-glucopyranoside

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 1h;
D-Fructose
57-48-7

D-Fructose

ammonium chloride

ammonium chloride

ammonia
7664-41-7

ammonia

A

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

B

2-amino-2-deoxy-ξ-D-glucosylamine

2-amino-2-deoxy-ξ-D-glucosylamine

Conditions
ConditionsYield
at 100℃;
hydrogenchloride
7647-01-0

hydrogenchloride

ethanol
64-17-5

ethanol

D-glucosaminic acid
3646-68-2

D-glucosaminic acid

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
und darauffolgende Reduktion mit Natriumamalgam;
2-benzylamino-2-deoxy-glucononitrile

2-benzylamino-2-deoxy-glucononitrile

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With hydrogenchloride; palladium Hydrogenation;
chitin

chitin

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
durch Spaltung;
With hydrogenchloride
claw of a lobster

claw of a lobster

armor plate of a lobster

armor plate of a lobster

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With hydrogenchloride
conalbumin

conalbumin

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

d-glucosaminoic acid

d-glucosaminoic acid

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With hydrogenchloride; ethanol anschliessend Behandeln mit Natriumamalgam und Schwefelsaeure;
egg yolk

egg yolk

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

euglobulin

euglobulin

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

glucoprotein

glucoprotein

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With acid
liverprotein

liverprotein

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

membrane substance of fungus

membrane substance of fungus

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With hydrogenchloride Hydrolysis;
mucoide

mucoide

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
Hydrolysis.aus Ascites-Fluessigkeit;
myxom-mucin

myxom-mucin

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
Hydrolysis;
ovalbumin

ovalbumin

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

ovomucoid

ovomucoid

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With acid
paramucin

paramucin

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With acid
protein

protein

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With acid Bildet sich besonders aus Glykoproteiden: so aus den Mucinen des Sputums und der Submaxillardruese;
durch Spaltung;
pseudomucin

pseudomucin

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With acid
serum-albumin

serum-albumin

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With alkali
serum-globulin

serum-globulin

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

serum mucoide

serum mucoide

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With acid
shell of a lobster

shell of a lobster

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With hydrogenchloride
shell of crayfish

shell of crayfish

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

Conditions
ConditionsYield
With hydrogenchloride
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

C43H51N7O9S2

C43H51N7O9S2

(x)C6H13NO5*C43H51N7O9S2

(x)C6H13NO5*C43H51N7O9S2

Conditions
ConditionsYield
In methanol at 20℃; for 7h;99.61%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

2-amino-2-deoxy-D-glucose propane-1,3-diyldithioacetal hydrochloride
72022-71-0

2-amino-2-deoxy-D-glucose propane-1,3-diyldithioacetal hydrochloride

Conditions
ConditionsYield
With hydrogenchloride 1.) 0 degC, 2 h, 2.) 60 degC, 12 h;92%
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

(fluorenylmethoxy)carbonyl chloride
28920-43-6

(fluorenylmethoxy)carbonyl chloride

acetic anhydride
108-24-7

acetic anhydride

Acetic acid (3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-4-yl ester
1040868-13-0

Acetic acid (3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-tetrahydro-pyran-4-yl ester

Conditions
ConditionsYield
Stage #1: 2-amino-2-deoxyglucose; (fluorenylmethoxy)carbonyl chloride With sodium hydrogencarbonate In 1,4-dioxane; water for 1h;
Stage #2: acetic anhydride With pyridine for 12h;
91%
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

C14H16N4O6
1598423-52-9

C14H16N4O6

C14H16N4O6*C6H13NO5
1598423-54-1

C14H16N4O6*C6H13NO5

Conditions
ConditionsYield
In water at 20℃;90.57%
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

C27H31N2O2Si(1+)

C27H31N2O2Si(1+)

C33H42N3O6Si(1+)

C33H42N3O6Si(1+)

Conditions
ConditionsYield
Stage #1: C27H31N2O2Si(1+) With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: 2-amino-2-deoxyglucose In N,N-dimethyl-formamide at 20℃; for 1h;
85.8%
1,3-dimethylbarbituric acid
769-42-6

1,3-dimethylbarbituric acid

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

5-((1S,2S,3R,4S,5R)-2-Amino-1,3,4,5,6-pentahydroxy-hexyl)-6-hydroxy-1,3-dimethyl-1H-pyrimidine-2,4-dione

5-((1S,2S,3R,4S,5R)-2-Amino-1,3,4,5,6-pentahydroxy-hexyl)-6-hydroxy-1,3-dimethyl-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
In water at 50℃;85%
Benzofuran-2-carboxylic acid
496-41-3

Benzofuran-2-carboxylic acid

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2Hpyran-3-yl)benzofuran-2-carboxamide

N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2Hpyran-3-yl)benzofuran-2-carboxamide

Conditions
ConditionsYield
Stage #1: Benzofuran-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In acetonitrile
Stage #2: 2-amino-2-deoxyglucose In acetonitrile at 30℃; for 0.833333h; Temperature; Solvent; Time;
85%
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

C45H33N5S

C45H33N5S

C51H46N6O5S

C51H46N6O5S

Conditions
ConditionsYield
With dicarbonate In water; dimethyl sulfoxide at 20℃; for 5h; pH=9;83%
butanoic acid anhydride
106-31-0

butanoic acid anhydride

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

N-butyrylglucosamine
63223-56-3

N-butyrylglucosamine

Conditions
ConditionsYield
In methanol at 0 - 20℃; for 24h;80%
5-methylbenzofuran-2-carboxylic acid
10242-09-8

5-methylbenzofuran-2-carboxylic acid

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

5-methyl-N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carboxamide

5-methyl-N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carboxamide

Conditions
ConditionsYield
Stage #1: 5-methylbenzofuran-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In acetonitrile
Stage #2: 2-amino-2-deoxyglucose In acetonitrile for 0.833333h; Heating;
77%
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

5-fluorobenzofuran-2-carboxylic acid
89197-62-6

5-fluorobenzofuran-2-carboxylic acid

5-fluoro-N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carboxamide

5-fluoro-N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carboxamide

Conditions
ConditionsYield
Stage #1: 5-fluorobenzofuran-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In acetonitrile
Stage #2: 2-amino-2-deoxyglucose In acetonitrile for 0.833333h; Heating;
76%
5-methoxybenzofuran-2-carboxylic acid
10242-08-7

5-methoxybenzofuran-2-carboxylic acid

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

5-methoxy-N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carboxamide

5-methoxy-N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carboxamide

Conditions
ConditionsYield
Stage #1: 5-methoxybenzofuran-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In acetonitrile
Stage #2: 2-amino-2-deoxyglucose In acetonitrile for 0.833333h; Heating;
72%
BARBITURIC ACID
67-52-7

BARBITURIC ACID

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

5-((1S,2S,3R,4S,5R)-2-Amino-1,3,4,5,6-pentahydroxy-hexyl)-6-hydroxy-1H-pyrimidine-2,4-dione

5-((1S,2S,3R,4S,5R)-2-Amino-1,3,4,5,6-pentahydroxy-hexyl)-6-hydroxy-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
In water at 50℃;70%
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

C27H22F2N2O6

C27H22F2N2O6

C29H30F2N2O8

C29H30F2N2O8

Conditions
ConditionsYield
With pyridine at 90℃; for 3h;68%
6-methoxybenzofuran-2-carboxylic acid
50551-61-6

6-methoxybenzofuran-2-carboxylic acid

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

6-methoxy-N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carboxamide

6-methoxy-N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carboxamide

Conditions
ConditionsYield
Stage #1: 6-methoxybenzofuran-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In acetonitrile
Stage #2: 2-amino-2-deoxyglucose In acetonitrile for 0.833333h; Heating;
68%
7-methoxybenzofuran-2-carboxylic acid
4790-79-8

7-methoxybenzofuran-2-carboxylic acid

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

7-methoxy-N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carboxamide

7-methoxy-N-(2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)benzofuran-2-carboxamide

Conditions
ConditionsYield
Stage #1: 7-methoxybenzofuran-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In acetonitrile
Stage #2: 2-amino-2-deoxyglucose In acetonitrile for 0.833333h; Heating;
64%
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

[Cl2Pt(6-aminocaproic acid)2]

[Cl2Pt(6-aminocaproic acid)2]

C24H48Cl2N4O12Pt

C24H48Cl2N4O12Pt

Conditions
ConditionsYield
Stage #1: [Cl2Pt(6-aminocaproic acid)2] With 1-hydroxy-pyrrolidine-2,5-dione; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at -10 - 20℃; for 16h;
Stage #2: 2-amino-2-deoxyglucose With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 17h;
46%
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

C21H24N6O6

C21H24N6O6

C27H35N7O10

C27H35N7O10

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h;44%
3-(4-nitrophenyl)-propenal
49678-08-2

3-(4-nitrophenyl)-propenal

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

2-(4-nitro-trans-cinnamylidenamino)-2-deoxy-D-glucose

2-(4-nitro-trans-cinnamylidenamino)-2-deoxy-D-glucose

butanoic acid anhydride
106-31-0

butanoic acid anhydride

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

N-butyryl α-glucosamine
15961-60-1

N-butyryl α-glucosamine

Conditions
ConditionsYield
With methanol
formic acid
64-18-6

formic acid

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

2-deoxy-2-formamido-β-D-glucopyranose
6905-58-4

2-deoxy-2-formamido-β-D-glucopyranose

Conditions
ConditionsYield
With acetic anhydride
3-bromobenzoyl chloride
1711-09-7

3-bromobenzoyl chloride

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

2-(3-bromo-benzoylamino)-2-deoxy-D-glucose
150698-52-5

2-(3-bromo-benzoylamino)-2-deoxy-D-glucose

2,4-dichloro-1,5-dinitrobenzene
3698-83-7

2,4-dichloro-1,5-dinitrobenzene

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

2-(5-chloro-2,4-dinitro-anilino)-2-deoxy-D-glucose

2-(5-chloro-2,4-dinitro-anilino)-2-deoxy-D-glucose

Conditions
ConditionsYield
With ethanol
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

CYANAMID
420-04-2

CYANAMID

A

(R)-1-((3aS)-2-amino-6c-hydroxy-(3ar,6ac)-3a,5,6,6a-tetrahydro-1H-furo[2,3-d]imidazol-5c-yl)-ethane-1,2-diol
46318-31-4

(R)-1-((3aS)-2-amino-6c-hydroxy-(3ar,6ac)-3a,5,6,6a-tetrahydro-1H-furo[2,3-d]imidazol-5c-yl)-ethane-1,2-diol

B

D-(1R)-1-(2-amino-1(3)H-imidazol-4-yl)-erythritol
46292-62-0

D-(1R)-1-(2-amino-1(3)H-imidazol-4-yl)-erythritol

Conditions
ConditionsYield
With aqueous solution of pH 7
2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

hydrazinecarbodithioic acid methyl ester
5397-03-5

hydrazinecarbodithioic acid methyl ester

2-(N'-methylsulfanylthiocarbonyl-hydrazino)-2-deoxy-D-glucose-(methylsulfanylthiocarbonyl-hydrazone)

2-(N'-methylsulfanylthiocarbonyl-hydrazino)-2-deoxy-D-glucose-(methylsulfanylthiocarbonyl-hydrazone)

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

S-ethyl-dithiocarbazate
14803-66-8

S-ethyl-dithiocarbazate

2-(N'-ethylsulfanylthiocarbonyl-hydrazino)-2-deoxy-D-glucose-(ethylsulfanylthiocarbonyl-hydrazone)

2-(N'-ethylsulfanylthiocarbonyl-hydrazino)-2-deoxy-D-glucose-(ethylsulfanylthiocarbonyl-hydrazone)

3416-24-8Relevant articles and documents

Brasilane sesquiterpenoids and alkane derivatives from cultures of the basidiomycete Coltricia sideroides

Hu, Dong-Bao,Zhang, Shen,He, Jiang-Bo,Dong, Ze-Jun,Li, Zheng-Hui,Feng, Tao,Liu, Ji-Kai

, p. 50 - 54 (2015)

Three new brasilane-type sesquiterpenoids, brasilanes A-C (1-3), together with two new alkane derivatives, colisiderin A (4) and 7(E),9(E)-undecandiene-2,4,5-triol (5), were isolated from cultures of the basidiomycete Coltricia sideroides. Their structures were elucidated by NMR and MS data analyses. The absolute configuration of 4 was determined by TDDFT ECD calculations while brasilane-type sesquiterpenoids were isolated from cultures of mushroom for the first time. Compounds 2 and 4 showed weak cytotoxicities against HL-60 and SW480, respectively.

The structure of the O-antigen of Cronobacter sakazakii HPB 2855 isolate involved in a neonatal infection

MacLean, Leann L.,Vinogradov, Evgeny,Pagotto, Franco,Farber, Jeffrey M.,Perry, Malcolm B.

, p. 1932 - 1937 (2010)

Strains of Cronobacter sakazakii (previously known as Enterobacter sakazakii) are medically recognized important Gram-negative bacterial pathogens that cause enterocolitis, septicemia, and meningitis, with a high mortality rate in neonates. The structure of their O-antigens, that form part of their somatic lipopolysaccharide (LPS) components, is of interest for their chemical and serological identification and their relationship to virulence. The O-polysaccharide (O-PS) of C. sakazakii HPB 2855 (SK 81), a strain isolated from an infant at the Hospital for Sick Children in Toronto in 1981, was shown to be a polymer of a partially O-acetylated-repeating hexasaccharide unit composed of d-glucose, d-galacturonic acid, 2-acetamido-2-deoxy-d-galactose, and l-rhamnose (1:1:1:3). From composition and methylation analysis, and the application of 1D and 2D 1H and 13C NMR spectroscopy, the O-PS was determined to be a polymer of a repeating oligosaccharide unit having the structure: [figure persented]

Triterpenoid saponins from Piptadeniastrum africanum (Hook. f.) Brenan

Noté, Olivier Placide,Tapondjou, Azefack Léon,Mitaine-Offer, Anne-Claire,Miyamoto, Tomofumi,Pegnyemb, Dieudonné Emmanuel,Lacaille-Dubois, Marie-Aleth

, p. 505 - 510 (2013)

One new triterpenoid saponin, named piptadeniaoside (1), along with two known saponins (2-3) have been isolated from the stem bark of Piptadeniastrum africanum. After previous isolation of flavone derivatives from this plant, new phytochemical investigati

Simplified determination of the content and average degree of acetylation of chitin in crude black soldier fly larvae samples

D'Hondt, Els,Soetemans, Lise,Bastiaens, Leen,Maesen, Miranda,Jespers, Vincent,Van den Bosch, Bert,Voorspoels, Stefan,Elst, Kathy

supporting information, (2020/01/25)

Insects are considered a promising alternative protein source for food and feed, but contain significant amounts of chitin, often undesirable due to indigestibility, disagreeable texture and negative effect on nutrients intake. Fractionation strategies are thus increasingly being applied to isolate and valorize chitin separately. The analysis of chitin generally requires an intensive pretreatment to remove impurities, and derivatization to generate sufficient detector response. In this work, a liquid chromatography method, without pretreatment nor derivatization, was developed for the simultaneous determination of chitin content and degree of acetylation in non-purified samples of black soldier fly (BSF) larvae. The method is found to be more suitable, compared to traditional methods, for assessing high degrees of acetylation. For the first time, the degree of acetylation of BSF chitin (81 ± 2%) is reported. Additionally, the chitin content of BSF soft tissues is estimated at approximately 20% of the total chitin content (8.5 ± 0.1%).

Enzymatic production of fully deacetylated chitooligosaccharides and their neuroprotective and anti-inflammatory properties

Santos-Moriano,Fernandez-Arrojo,Mengibar,Belmonte-Reche,Pe?alver,Acosta,Ballesteros,Morales,Kidibule,Fernandez-Lobato,Plou, Francisco J.

, p. 57 - 67 (2017/09/30)

Among several commercial enzymes screened for chitosanolytic activity, Neutrase 0.8L (a protease from Bacillus amyloliquefaciens) was selected in order to obtain a product enriched in deacetylated chitooligosaccharides (COS). The hydrolysis of different chitosans with this enzyme was followed by size exclusion chromatography (SEC-ELSD), mass spectrometry (ESI-Q-TOF), and high-performance anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD). Neutrase 0.8L converted 10?g/L of various chitosans into mostly deacetylated oligosaccharides, yielding approximately 2.5?g/L of chitobiose, 4.5?g/L of chitotriose, and 3?g/L of chitotetraose. We found out that the neutral protease was not responsible for the chitosanolytic activity in the extract, while it could participate in the deacetylating process. The synthesized COS were tested in vitro for their neuroprotective (toward human SH-S5Y5 neurons) and anti-inflammatory (in RAW macrophages) activities, and compared with other functional ingredients, namely fructooligosaccharides.

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