187269-63-2 Usage
Description
2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosyl fluoride, with the CAS number 187269-63-2, is a versatile and valuable chiral building block in the field of organic chemistry. It is specifically utilized for stereospecific α-D-mannosylations, which are crucial in the synthesis of complex carbohydrate structures and their derivatives. 2,3,4,6-Tetra-O-pivaloyl-D-mannopyranosylfluoride is characterized by its unique structure, which features four pivaloyl groups protecting the hydroxyl groups at the 2, 3, 4, and 6 positions of the D-mannopyranosyl core. The presence of these protective groups allows for selective reactions and enhances the stability of the molecule during various synthetic processes.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 187269-63-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,8,7,2,6 and 9 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 187269-63:
(8*1)+(7*8)+(6*7)+(5*2)+(4*6)+(3*9)+(2*6)+(1*3)=182
182 % 10 = 2
So 187269-63-2 is a valid CAS Registry Number.
187269-63-2Relevant articles and documents
Stereospecific α-D-mannosylation
Scott, Ian L.,Market, Robert V.,DeOrazio, Russell J.,Meckler, Harold,Kogan, Timothy P.
, p. 210 - 216 (2007/10/03)
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.
