53784-29-5

Basic information

• Product Name: 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYL AZIDE
• Synonyms: 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYL AZIDE;ALPHA-D-MANNOPYRANOSYL AZIDE TETRAACETATE;2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl azide;α-D-Mannopyranosyl azide tetraacetate
• CAS NO: 53784-29-5
• Molecular Formula: C₁₄H₁₉N₃O₉
• Molecular Weight: 373.32
• Mol File: 53784-29-5.mol
• Article Data: 30

Chemical Properties

• Melting Point: 103-105 °C
• Appearance: /
• Storage Temp.: −20°C
• CAS DataBase Reference: 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYL AZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYL AZIDE(53784-29-5)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-ACETYL-ALPHA-D-MANNOPYRANOSYL AZIDE(53784-29-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 53784-29-5(Hazardous Substances Data)

Usage

General Description

2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranosyl azide is a chemical compound commonly used in organic synthesis and chemical biology. It is often utilized as a precursor for the synthesis of various glycosides and glycoconjugates due to its ability to easily undergo a variety of chemical reactions. Its acetylated form makes it more stable and less reactive, making it a valuable tool in the modification of carbohydrates and the study of glycosylation processes. Additionally, its azide moiety can be readily transformed into other functional groups, further expanding its synthetic utility. Due to its versatility and ability to be employed in a wide range of chemical transformations, 2,3,4,6-Tetra-O-acetyl-alpha-D-mannopyranosyl azide is a valuable compound in chemical research and development.

Upstream product

• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide 
• 121238-27-5 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate 
• 83-87-4 D-Mannose pentaacetate 
• 4648-54-8 trimethylsilylazide 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 60619-58-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide 
• 13242-53-0 acetobromomannose 
• 530-26-7 D-Mannose 
• 108-24-7 acetic anhydride 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 139710-25-1 (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-((diphenoxyphosphoryl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 

Relevant articles and documents

Does targeting Arg98 of FimH lead to high affinity antagonists?

Bacterial resistance has become an important challenge in the treatment of urinary tract infections. The underlying resistance mechanisms can most likely be circumvented with an antiadhesive approach, antagonizing the lectin FimH located at the tip of fim

Glycoconjugated Metallohelices have Improved Nuclear Delivery and Suppress Tumour Growth In Vivo

Monosaccharides are added to the hydrophilic face of a self-assembled asymmetric FeII metallohelix, using CuAAC chemistry. The sixteen resulting architectures are water-stable and optically pure, and exhibit improved antiproliferative selectivity against colon cancer cells (HCT116 p53+/+) with respect to the non-cancerous ARPE-19 cell line. While the most selective compound is a glucose-appended enantiomer, its cellular entry is not mainly glucose transporter-mediated. Glucose conjugation nevertheless increases nuclear delivery ca 2.5-fold, and a non-destructive interaction with DNA is indicated. Addition of the glucose units affects the binding orientation of the metallohelix to naked DNA, but does not substantially alter the overall affinity. In a mouse model, the glucose conjugated compound was far better tolerated, and tumour growth delays for the parent compound (2.6 d) were improved to 4.3 d; performance as good as cisplatin but with the advantage of no weight loss in the subjects.

Synthesis of biurets: Via TMSNCO addition to 1-aminosugars: Application in the de novo synthesis of dC oxidation products

The reaction between 1-aminosugars and trimethylisocyanate (TMSNCO) was optimised as a one-step synthetic strategy for the synthesis of sugar biurets. This protocol was successfully applied to a number of 1-aminosugars, which exclusively provided the corresponding biurets in 67-99% yields. The new methodology was applied in the de novo synthesis of N1-(2-deoxy-α/β-d-erythro-pentofuranosyl)biuret (dfBU) and N1-(2-deoxy-α/β-d-erythro-pentopyranosyl)biuret (dpBU), two known DNA lesions arising from the hydroxyl radical induced decomposition of 2′-deoxycytidine (dCyd).