1,3,4,6-tetra-o-acetyl-2-azido-2-deoxyglucopyranose profile

## 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxyglucopyranose: A Versatile Building Block in Chemistry

1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxyglucopyranose, often shortened to **tetraacetylazidoglucose**, is a synthetic carbohydrate derivative. It's a crucial building block in organic chemistry, especially for the synthesis of complex carbohydrates, glycoconjugates, and other biologically relevant molecules.

Here's a breakdown of its features and importance:

**Structure:**

* **Glucopyranose core:** The molecule is based on the D-glucopyranose sugar, a six-membered ring.
* **2-Azido group:** The hydroxyl group at position 2 is replaced with an azido group (-N3), making it a potential reactive site.
* **Acetylation:** The hydroxyl groups at positions 1, 3, 4, and 6 are protected with acetyl groups (-COCH3). This protection is important for controlling reactivity and selectivity during synthesis.

**Importance in Research:**

* **Glycosylation reactions:** The azido group can be easily transformed into an amine (-NH2) group via a **Staudinger reduction**, creating a versatile handle for attaching other molecules. This makes it an excellent starting point for building complex carbohydrate structures.
* **Glycoconjugate synthesis:** Tetradeacetylazidoglucose can be linked to other molecules, such as proteins, lipids, or nucleic acids, to create glycoconjugates. These conjugates are essential for studying the interactions between carbohydrates and biological systems.
* **Drug development:** The ability to synthesize complex carbohydrates using tetraacetylazidoglucose opens up opportunities for developing new drugs that target carbohydrate-mediated processes. For instance, it can be used to design inhibitors of enzymes that use carbohydrates as substrates.
* **Materials science:** This compound can be incorporated into materials for various applications, including biocompatible polymers and functionalized surfaces.

**Overall, 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxyglucopyranose plays a significant role in various fields by providing a versatile platform for synthesizing complex carbohydrate-related compounds. Its unique combination of reactivity and protection allows for efficient and controllable modification, making it a valuable tool in chemical research and development.**

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxyglucopyranose: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	133445
SCHEMBL ID	15665548
MeSH ID	M0191784

Synonym
1,3,4,6-tetra-o-acetyl-2-azido-2-deoxyglucopyranose
beta-d-glucopyranose, 2-azido-2-deoxy-, 1,3,4,6-tetraacetate
taad
80321-89-7
T2196
1,3,4,6-tetra-o-acetyl-2-azido-2-deoxy-beta-d-glucopyranose
[(2r,3s,4r,5r,6s)-3,4,6-triacetyloxy-5-azidooxan-2-yl]methyl acetate
2-azido-2-deoxy-1,3,4,6-tetra-o-acetyl-beta-d-glucopyranose
AKOS025295772
QKGHBQJLEHAMKJ-DHGKCCLASA-N
1,3,4,6-tetra-o-acetyl-2-azido-2-deoxy-b-d-glucopyranose
W-203836
SCHEMBL15665548
GS-8025
[(2r,3s,4r,5r,6s)-3,4,6-tris(acetyloxy)-5-azidooxan-2-yl]methyl acetate
T72956
2-azido-b-d-glucose tetraacetate
2-azido-2-deoxy-3,4,6-tri-o-acetyl-b-d-glucopyranosyl acetate
DTXSID701001163
1,3,4,6-tetra-o-acetyl-2-azido-2-deoxyhexopyranose

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	1 (2.70)	18.2507
2000's	0 (0.00)	29.6817
2010's	1 (2.70)	24.3611
2020's	35 (94.59)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	1 (2.70%)	5.53%
Reviews	6 (16.22%)	6.00%
Case Studies	1 (2.70%)	4.05%
Observational	1 (2.70%)	0.25%
Other	28 (75.68%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	2.6	1	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	2.6	1	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
aminopropionitrile Aminopropionitrile: Reagent used as an intermediate in the manufacture of beta-alanine and pantothenic acid.	3.46	4	aminopropionitrile	antineoplastic agent; antirheumatic drug; collagen cross-linking inhibitor; plant metabolite
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	2.6	1	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
uridine diphosphate glucose Uridine Diphosphate Glucose: A key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acid. Also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.. UDP-alpha-D-glucose : The alpha-anomer of UDP-alpha-D-glucose. It is used in nucleotide sugars metabolism.	2.15	1	UDP-D-glucose	fundamental metabolite
mannose mannopyranose : The pyranose form of mannose.	1.97	1	D-aldohexose; D-mannose; mannopyranose	metabolite
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	4.61	4	pseudohalide anion	mitochondrial respiratory-chain inhibitor
oltipraz oltipraz : A 1,2-dithiole that is 3H-1,2-dithiole-3-thione substituted at positions 4 and 5 by methyl and pyrazin-2-yl groups respectively.	2.41	1	1,2-dithiole; pyrazines	angiogenesis modulating agent; antimutagen; antineoplastic agent; antioxidant; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; neurotoxin; protective agent; schistosomicide drug
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	4.61	4
senkyunolide i senkyunolide I: has antioxidant and anti-migraine activities; isolated from Ligusticum chuanxiong; structure in first source	2.6	1
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.6	1	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger

Condition	Relationship Strength	Studies	Trials
Aneurysm, Thoracic Aortic [description not available]	9.3	27	0
Aortic Dissection [description not available]	11.26	42	1
Aortic Aneurysm, Thoracic An abnormal balloon- or sac-like dilatation in the wall of the THORACIC AORTA. This proximal descending portion of aorta gives rise to the visceral and the parietal branches above the aortic hiatus at the diaphragm.	9.3	27	0
Marfan Syndrome, Type I [description not available]	3.81	2	0
Marfan Syndrome An autosomal dominant disorder of CONNECTIVE TISSUE with abnormal features in the heart, the eye, and the skeleton. Cardiovascular manifestations include MITRAL VALVE PROLAPSE, dilation of the AORTA, and aortic dissection. Other features include lens displacement (ectopia lentis), disproportioned long limbs and enlarged DURA MATER (dural ectasia). Marfan syndrome (type 1) is associated with mutations in the gene encoding FIBRILLIN-1 (FBN1), a major element of extracellular microfibrils of connective tissue. Mutations in the gene encoding TYPE II TGF-BETA RECEPTOR (TGFBR2) are associated with Marfan syndrome type 2.	3.81	2	0
Blood Loss, Postoperative [description not available]	2.41	1	0
Endoleak Postoperative hemorrhage from an endovascular AORTIC ANEURYSM repaired with endoluminal placement of stent grafts (BLOOD VESSEL PROSTHESIS IMPLANTATION). It is associated with pressurization, expansion, and eventual rupture of the aneurysm.	3.33	1	0
MODS [description not available]	2.41	1	0
Multiple Organ Failure A progressive condition usually characterized by combined failure of several organs such as the lungs, liver, kidney, along with some clotting mechanisms, usually postinjury or postoperative.	2.41	1	0
Apoplexy [description not available]	2.41	1	0
Hemorrhagic Stroke Stroke due to rupture of a weakened blood vessel in the brain (e.g., CEREBRAL HEMISPHERES; CEREBELLUM; SUBARACHNOID SPACE).	2.41	1	0
Ischemia A hypoperfusion of the BLOOD through an organ or tissue caused by a PATHOLOGIC CONSTRICTION or obstruction of its BLOOD VESSELS, or an absence of BLOOD CIRCULATION.	2.9	2	0
Stroke A group of pathological conditions characterized by sudden, non-convulsive loss of neurological function due to BRAIN ISCHEMIA or INTRACRANIAL HEMORRHAGES. Stroke is classified by the type of tissue NECROSIS, such as the anatomic location, vasculature involved, etiology, age of the affected individual, and hemorrhagic vs. non-hemorrhagic nature. (From Adams et al., Principles of Neurology, 6th ed, pp777-810)	2.41	1	0
Fusiform Aneurysm Elongated, spindle-shaped dilation in the wall of blood vessels, usually large ARTERIES with ATHEROSCLEROSIS.	2.41	1	0
Aneurysm Pathological outpouching or sac-like dilatation in the wall of any blood vessel (ARTERIES or VEINS) or the heart (HEART ANEURYSM). It indicates a thin and weakened area in the wall which may later rupture. Aneurysms are classified by location, etiology, or other characteristics.	2.41	1	0
Complication, Postoperative [description not available]	3.86	6	0
Postoperative Complications Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery.	3.86	6	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.01	2	0
Acute Kidney Failure [description not available]	3.3	3	0
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	3.3	3	0
Aneurysm, Aortic [description not available]	5.65	5	0
Aortic Aneurysm An abnormal balloon- or sac-like dilatation in the wall of AORTA.	5.65	5	0
Hyperuricemia Excessive URIC ACID or urate in blood as defined by its solubility in plasma at 37 degrees C; greater than 0.42mmol per liter (7.0mg/dL) in men or 0.36mmol per liter (6.0mg/dL) in women. This condition is caused by overproduction of uric acid or impaired renal clearance. Hyperuricemia can be acquired, drug-induced or genetically determined (LESCH-NYHAN SYNDROME). It is associated with HYPERTENSION and GOUT.	2.6	1	0
Inferior Dislocation [description not available]	2.6	1	0
Conus Medullaris Syndrome [description not available]	2.6	1	0
Blood Clot [description not available]	2.6	1	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	2.6	1	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.6	1	0
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	2.6	1	0
Aortic Diseases Pathological processes involving any part of the AORTA.	3.52	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	3.52	1	0

1,3,4,6-tetra-o-acetyl-2-azido-2-deoxyglucopyranose

Description

Cross-References

Synonyms (20)

Research

Studies (37)

Market Indicators

Research Demand Index: 13.25

Study Types