18933-88-5

Usage

Uses

Used in Chemical Biology Research:
a-D-Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxyis used as a probe for studying carbohydrate interactions in chemical biology research. Its unique structure allows for the investigation of the roles of carbohydrates in various biological processes.
Used in Biochemistry Research:
In biochemistry, a-D-Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxyserves as a precursor for synthesizing glycoconjugates. Its ability to be selectively modified using click chemistry makes it a valuable tool for exploring complex carbohydrate structures and their functions in biological systems.
Used in Click Chemistry:
a-D-Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxyis used as a versatile building block in click chemistry. The azido group present in the compound enables selective modification with other functional groups, facilitating the synthesis of diverse carbohydrate-based structures for various applications in chemical and biological research.
Used in Pharmaceutical Industry:
a-D-Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxyis used as a key intermediate in the synthesis of carbohydrate-based drugs. Its unique properties and reactivity make it a promising candidate for the development of novel therapeutic agents targeting carbohydrate-related diseases.
Used in Diagnostics:
a-D-Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxycan be employed as a diagnostic tool in the detection and analysis of carbohydrate-related disorders. Its ability to selectively interact with specific carbohydrate structures makes it a valuable component in the development of diagnostic assays and tests.
Overall, a-D-Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxyhas important applications in various fields, including chemical biology, biochemistry, click chemistry, pharmaceuticals, and diagnostics, due to its unique structure and reactivity.

Upstream product

• 99-20-7 TREHALOSE 
• 23103-34-6 2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranosyl-(1→1)-2,3,4-tri-O-acetyl-6-azido-6-deoxy-α-D-glucopyranoside 
• 18933-87-4 6,6'-diazido-2,2',3,3',4,4'-hexa-O-benzoyl-6,6'-dideoxy-α,α-D-trehalose 
• 67398-72-5 2,2',3,3',4,4'-hexa-O-acetyl-α,α'-trehalose 
• 18929-82-3 4,6;4',6'-di-O-benzylidene-α,α-D-trehalose 
• 42390-78-3 2,3,4,6,2',3',4',6'-octa-O-trimethylsilyl-α,α-D-trehalose 
• 59578-12-0 2,3,4,2’,3’,4’-hexakis-O-(trimethylsilyl)-α,α-trehalose 
• 23089-74-9 2,2',3,3',4,4'-hexa-O-acetyl-6,6'-bis-O-(4-toluenesulfonyl)-α,α'-trehalose 
• 577969-86-9 2,3,2',3'-tetra-O-benzoyl-4,6:4',6'-di-O-benzylidene-α,α-trehalose 
• 42891-34-9 2,2',3,3',4,4'-hex-O-acetyl-6,6'-dideoxy-6,6'-dibromo-α,α-D-trehalose 
• 23089-73-8 2,2',3,3',4,4'-hexa-O-acetyl-6,6'-bis-O-methylsulfonyl-α,α'-trehalose 
• 52290-50-3 6,6′-dideoxy-6,6′-diiodo-α,α′-trehalose 
• 18933-86-3 6,6'-dibromo-2,3,4,2',3',4'-hexa-O-benzoyl-6,6'-dideoxy-α,α-trehalose 
• 50257-21-1 2,3,4,2',3',4'-hexa-O-acetyl-6,6'-dichloro-6,6'-dideoxy-α,α-trehalose 

Downstream Products

• 30923-00-3 6,6'-diamino-6,6'-dideoxy-α,α-D-trehalose 
• 76790-49-3 6,6'-diacetamido-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose 
• 76790-48-2 6,6'-diamino-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose 
• 1581698-79-4 C₆₄H₇₈N₁₂O₁₁ 

Relevant academic research and scientific papers

Supramolecular structures of substituted α,α′-trehalose derivatives

The structures of five substituted α,α′-trehalose trehalose derivatives have been determined, and these are compared with those of four previously published analogues. In 2,2′,3,3′,4,4′- hexaacetato-6,6′-bis-O-methylsulfonyl-α,α′-trehalose, C26

Improved synthesis of 6-azido-6-deoxy- and 6,6′-diazido-dideoxy- α,α-trehaloses

An efficient synthesis of 6-azido-6-deoxy and 6,6′-diazido-dideoxy- α,α-trehalose derivatives was achieved by reaction of trifluoromethanesulfonic anhydride with partially trimethylsilylated heptakis- and hexakis-O-(trimethylsilyl)-α,α-trehalose in the pr

Amide-linked brartemicin glycolipids exhibit Mincle-mediated agonist activity in vitro

Lipidated derivatives of the natural product brartemicin show much promise as vaccine adjuvants due to their ability to signal through the Macrophage Inducible C-type Lectin (Mincle). We synthesised three lipophilic amide-linked brartemicin derivatives and compared their agonist activity to that of their ester-linked counterparts in vitro. We demonstrate that the brartemicin amide derivatives activate bone-marrow-derived macrophages (BMDMs) in a Mincle-dependent manner, as evidenced by the production of the pro-inflammatory cytokine IL-1β in wildtype but not Mincle-/- cells. The amide derivatives showed activity that was as good as, if not better than, their ester counterparts. Two of the amide derivatives, but none of the ester-derivatives, also led to the production of IL-1β by human-derived monocytes. As the production of IL-1β is a good indicator of vaccine adjuvanticity potential, these findings suggest that amide-linked brartemicin derivatives show particular promise as vaccine adjuvants.

Trehalose-based neuroprotective autophagy inducers

A small set of trehalose-centered putative autophagy inducers was rationally designed and synthesized, with the aim to identify more potent and bioavailable autophagy inducers than free trehalose, and to acquire information about their molecular mechanism

BRARTEMICIN ANALOGUES

The invention relates to brartemicin analogues of Formula (IV) and their uses. These compounds are potent Mincle agonists and Th1-stimulating vaccine adjuvants.

Red emitting neutral fluorescent glycoconjugates for membrane optical imaging

A family of neutral fluorescent probes was developed, mimicking the overall structure of natural glycolipids in order to optimize their membrane affinity. Nonreducing commercially available di- or trisaccharidic structures were connected to a push-pull ch

CuAAC-mediated diversification of aminoglycoside-arginine conjugate mimics by non-reducing di- and trisaccharides

Di- and triguanidinylation of trehalose, sucrose, and melizitose has been achieved via a Huisgen-cycloaddition approach. They can serve as aminoglycoside-arginine conjugate mimics, which has been demonstrated by their biological profiles in assays against

Flow chemistry kinetic studies reveal reaction conditions for ready access to unsymmetrical trehalose analogues

Monofunctionalization of trehalose, a widely-found symmetric plant disaccharide, was studied in a microreactor to give valuable kinetic insights that have allowed improvements in desymmetrization yields and the development of a reaction sequence for large scale monofunctionalizations that allow access to probes of trehalose's biological function.

Direct azidation of unprotected carbohydrates under Mitsunobu conditions using hydrazoic acid

A single step procedure for the direct and regioselective synthesis of carbohydrate azides from unprotected sugars using hydrazoic acid under Mitsunobu conditions is reported. A series of mono-, di-, or triazido polyhydroxylated systems are described.

α,α-Trehalose derivatives bearing guanidino groups as inhibitors to HIV-1 Tat-TAR RNA interaction in human cells

Replication of HIV-1 requires specific interactions of Tat protein with TAR RNA. Disruption of Tat-TAR RNA interaction could inhibit HIV-1 replication. Here four target compounds were designed and synthesized to bind to TAR RNA for blocking the interaction of Tat-TAR RNA. The core molecule 6,6 ′-diamino-6,6′-dideoxy-α,α- trehalose was obtained from selective bromination of, α,α-trehalose at C-6,6′, followed by acetylation, azide displacement, deacetylation, and reduction. Coupling of the core molecule with the protected amino acid, then deprotection and guanidinylation generated the novel α,α-trehalose derivatives. Their abilities to inhibit Tat-TAR RNA interaction in human cells were determined by a Tat-dependent HIV-1 LTR-driven CAT assays.