187269-63-2

Basic information

• Product Name: 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosylfluoride
• Synonyms: 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosylfluoride
• CAS NO: 187269-63-2
• Molecular Formula: C₂₆H₄₃FO₉
• Molecular Weight: 518.61
• Mol File: 187269-63-2.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 0-10°C
• CAS DataBase Reference: 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosylfluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosylfluoride(187269-63-2)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosylfluoride(187269-63-2)

Safety Data

• Hazardous Substances Data: 187269-63-2(Hazardous Substances Data)

Usage

Uses

Used in Carbohydrate Chemistry:
2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl fluoride is used as a chiral building block for stereospecific α-D-mannosylations. This application is essential in the synthesis of complex carbohydrate structures and their derivatives, which are vital components in various biological systems and have potential applications in pharmaceuticals, diagnostics, and materials science.
Used in the Preparation of Glycosides:
In the field of organic chemistry, 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl fluoride is used as a key intermediate in the preparation of diand trivalent phenyl-substituted glycosides. These glycosides serve as selectin inhibitors, which play a crucial role in modulating cellular adhesion and inflammation processes. The development of such inhibitors can have significant implications in the treatment of various diseases, including autoimmune disorders and cancer.
Used in Drug Development:
The compound is also utilized in the pharmaceutical industry for the development of novel drugs targeting selectin-mediated cellular interactions. By inhibiting these interactions, the compound can potentially be used in the treatment of conditions such as inflammation, thrombosis, and metastasis of cancer cells.
Used in Materials Science:
In the field of materials science, 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl fluoride can be employed in the synthesis of carbohydrate-based materials with unique properties. These materials can find applications in areas such as drug delivery, sensors, and biocompatible coatings.

Upstream product

• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 66888-27-5 penta-O-acetyl-D-mannose 
• 3282-30-2 pivaloyl chloride 
• 2713-54-4 α-D-mannopyranosyl fluoride 

Downstream Products

• 503312-29-6 2,3,4,6-tetra-O-pivaloyl-α-D-mannopyranose 
• 28541-77-7 4-bromophenyl α-D-mannopyranoside 
• 243120-93-6 4-bromophenyl tetra-O-pivaloyl-α-D-mannopyranoside 
• 243120-94-7 4-nitrobenzyl tetra-O-pivaloyl-α-D-mannopyranoside 

Relevant articles and documents

Stereospecific α-D-mannosylation

The stereospecific formation of α-D-mannosyl glycosidic linkages has been achieved in high yield using tetra-O-pivaloyl-α-D-mannopyranosyl fluoride and boron trifluoride diethyl etherate in dichloromethane. Examples of the α-D-mannosylation of primary, secondary, benzylic and phenolic hydroxyl groups are described. Copyright (C) 1999 Elsevier Science Ltd.

High yield stereospecific mannosylation

A process of preparing mannosylated alcohols or phenols in high chemical yield and purity using tetra-O-pivaloylmannosylfluoride and a Lewis acid catalyst.