18933-88-5

Basic information

• Product Name: a-D-Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxy-
• Synonyms: Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxy-, a-D- (8CI); 6,6'-Diazido-6,6'-dideoxytrehalose; Trehalose,6,6'-diazido-6,6'-dideoxy-
• CAS NO: 18933-88-5
• Molecular Formula: C12H20 N6 O9
• Molecular Weight: 392.326
• Mol File: 18933-88-5.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: a-D-Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: a-D-Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxy-(18933-88-5)
• EPA Substance Registry System: a-D-Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxy-(18933-88-5)

Safety Data

• Hazardous Substances Data: 18933-88-5(Hazardous Substances Data)

Usage

General Description

a-D-Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxy- is a compound that consists of two glucopyranoside molecules, each with an azido and deoxy functional group attached to the sixth carbon. a-D-Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxy- is a derivative of glucose and is commonly used in chemical biology and biochemistry research as a probe for studying carbohydrate interactions and as a precursor for synthesizing glycoconjugates. The azido group can be selectively modified with other functional groups using click chemistry, making this compound a valuable tool for studying complex carbohydrate structures and their roles in biological processes. Overall, a-D-Glucopyranoside,6-azido-6-deoxy-a-D-glucopyranosyl6-azido-6-deoxy- has important applications in chemical and biological research.

Upstream product

• 52290-49-0 6,6'-dichloro-6,6'-dideoxy-α,α-trehalose 
• 52290-50-3 6,6′-dideoxy-6,6′-diiodo-α,α′-trehalose 
• 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 
• 23089-73-8 2,2',3,3',4,4'-hexa-O-acetyl-6,6'-bis-O-methylsulfonyl-α,α'-trehalose 
• 67398-72-5 2,2',3,3',4,4'-hexa-O-acetyl-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 
• 18933-86-3 6,6'-dibromo-2,3,4,2',3',4'-hexa-O-benzoyl-6,6'-dideoxy-α,α-trehalose 
• 18929-82-3 4,6;4',6'-di-O-benzylidene-α,α-D-trehalose 
• 577969-86-9 2,3,2',3'-tetra-O-benzoyl-4,6:4',6'-di-O-benzylidene-α,α-trehalose 
• 23089-74-9 2,2',3,3',4,4'-hexa-O-acetyl-6,6'-bis-O-(4-toluenesulfonyl)-α,α'-trehalose 
• 50257-21-1 2,3,4,2',3',4'-hexa-O-acetyl-6,6'-dichloro-6,6'-dideoxy-α,α-trehalose 
• 59578-12-0 2,3,4,2’,3’,4’-hexakis-O-(trimethylsilyl)-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 
• 1581698-79-4 C₆₄H₇₈N₁₂O₁₁ 
• 76790-48-2 6,6'-diamino-2,3,4,2',3',4'-hexa-O-benzyl-6,6'-dideoxy-α,α-trehalose 

Relevant articles and documents

Concerning 2,3,4,2',3',4'-hexa-O-acetyl-6,6'-diamino-6,6'-dideoxy-α,α-trehalose

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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.

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.

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