4196-35-4 Usage
Description
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl bromide is a synthetic intermediate with a unique structure that features a glucose molecule with four benzyl groups attached to its hydroxyl groups and a bromine atom at the anomeric position. 2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosylbromide is widely used in organic synthesis and carbohydrate chemistry.
Uses
Used in Organic Synthesis:
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl bromide is used as a synthetic intermediate for the preparation of various complex organic compounds. Its unique structure allows for selective reactions and functional group manipulations, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Carbohydrate Chemistry:
In the field of carbohydrate chemistry, 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl bromide is used as a glycosyl donor for the synthesis of oligosaccharides and glycoconjugates. Its benzyl protecting groups can be selectively removed to facilitate the formation of glycosidic bonds, enabling the construction of complex carbohydrate structures.
Used in Glycoprotein Synthesis:
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl bromide is used as a precursor to prepare glycosyl phenylthiosulfonates (Glyco-PTS), which are novel reagents for glycoprotein synthesis. These reagents offer advantages such as high reactivity, mild reaction conditions, and compatibility with various protecting group strategies, making them valuable tools for the preparation of biologically relevant glycoproteins.
Used in Pharmaceutical Industry:
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl bromide is used as a key intermediate in the synthesis of glycoconjugate drugs, which are a class of pharmaceuticals that incorporate carbohydrate moieties into their structures. These drugs often exhibit improved pharmacokinetic properties, enhanced solubility, and increased stability compared to their non-glycosylated counterparts.
Used in Agrochemical Industry:
In the agrochemical industry, 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl bromide is used as a building block for the synthesis of glycosylated agrochemicals, such as pesticides and herbicides. The introduction of carbohydrate moieties can improve the solubility, bioavailability, and environmental compatibility of these compounds, leading to more effective and sustainable agricultural products.
Check Digit Verification of cas no
The CAS Registry Mumber 4196-35-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,1,9 and 6 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 4196-35:
(6*4)+(5*1)+(4*9)+(3*6)+(2*3)+(1*5)=94
94 % 10 = 4
So 4196-35-4 is a valid CAS Registry Number.
4196-35-4Relevant articles and documents
Halide-mediated regioselective 6-O-glycosylation of unprotected hexopyranosides with perbenzylated glycosyl bromide donors
Niedbal, Dominika Alina,Madsen, Robert
, p. 415 - 419 (2016)
The regio- and stereoselective glycosylation at the 6-position in 2,3,4,6-unprotected hexopyranosides has been investigated with dibutyltin oxide as the directing agent. Perbenzylated hexopyranosyl bromides were employed as the donors and the glycosylations were promoted by tetrabutylammonium bromide. The couplings were completely selective for both glucose and galactose donors and acceptors as long as the stannylene acetal of the acceptor was soluble in dichloromethane. This gave rise to a number of 1,2-cis-linked disaccharides in reasonable yields. Mannose donors and acceptors, on the other hand, did not react in the glycosylation under these conditions.
Indolylthio glycosides as effective building blocks for chemical glycosylation
Demchenko, Alexei V.,Shrestha, Ganesh,Panza, Matteo,Singh, Yashapal,Rath, Nigam P.
, p. 15885 - 15894 (2021/01/19)
The S-indolyl (SIn) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions including thiophilic and metal-assisted pathways. Understanding of the reaction pathways for the SIn moiety activation was achieved via the extended mechanistic study. Also reported is how the new SIn donors fit into selective activation strategies for oligosaccharide synthesis.
β-Selective C-Glycosylation and its Application in the Synthesis of Scleropentaside A
Boehlich, G. Jacob,Schützenmeister, Nina
supporting information, p. 5110 - 5113 (2019/03/17)
C-Glycosides are carbohydrates that bear a C?C bond to an aglycon at the anomeric center. Due to their high stability towards chemical and enzymatic hydrolysis, these compounds are widely used as carbohydrate mimics in drug development. Herein, we report a general and exclusively β-selective method for the synthesis of a naturally abundant acyl-C-glycosidic structural motif first found in the scleropentaside natural product family. A Corey–Seebach umpolung reaction as the key step in the synthesis of scleropentaside A and analogues enables the β-selective construction of the anomeric C?C bond starting from unprotected carbohydrates in only four steps. The one-pot approach is highly atom-efficient and avoids the use of toxic heavy metals.
