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Catalog Number:
41515
CAS Number:
74808-09-6
2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate
Purity:
≥ 98%
Synonym(s):
(2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl2,2,2-trichloroacetimidate
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Product Information

2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl trichloroacetimidate is a versatile glycosyl donor widely utilized in carbohydrate chemistry for the synthesis of complex oligosaccharides and glycoconjugates. This compound is particularly valued for its ability to facilitate glycosylation reactions, enabling researchers to construct intricate carbohydrate structures with precision. Its unique tetra-O-benzyl protection scheme enhances stability and solubility, making it an ideal choice for various synthetic applications.

In the pharmaceutical and biotechnological sectors, this compound plays a crucial role in the development of glycosylated drugs and vaccines, where carbohydrate moieties are essential for biological activity and efficacy. Additionally, its application extends to the synthesis of glycoproteins and glycolipids, which are vital in cell signaling and recognition processes. The trichloroacetimidate group provides a reactive site that promotes efficient coupling reactions, making it superior to other glycosyl donors in terms of yield and selectivity. Researchers and industry professionals can leverage this compound to streamline their synthetic pathways and enhance the functionality of their carbohydrate-based products.

Synonyms
(2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl2,2,2-trichloroacetimidate
CAS Number
74808-09-6
Purity
≥ 98%
Molecular Formula
C36H36Cl3NO6
Molecular Weight
685.03
MDL Number
MFCD03427010
PubChem ID
3504953
Melting Point
69 - 74 °C (Lit.)
Appearance
White to light yellow powder
Optical Rotation
[á]20/D = 58 ° (C = 0.4 in Chloroform)
Conditions
Store at ≤ -10 °C
General Information
Synonyms
(2R,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl2,2,2-trichloroacetimidate
CAS Number
74808-09-6
Purity
≥ 98%
Molecular Formula
C36H36Cl3NO6
Molecular Weight
685.03
MDL Number
MFCD03427010
PubChem ID
3504953
Melting Point
69 - 74 °C (Lit.)
Appearance
White to light yellow powder
Optical Rotation
[á]20/D = 58 ° (C = 0.4 in Chloroform)
Conditions
Store at ≤ -10 °C
Properties
Additional property information coming soon!
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Safety and Regulations
Hazmat
No
Antibiotic
No
DEA-regulated
No
Warnings
-
Applications

2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl trichloroacetimidate is widely utilized in research focused on:

  • Synthetic Chemistry: This compound serves as a key intermediate in the synthesis of glycosides and oligosaccharides, facilitating the development of complex carbohydrates for various applications.
  • Pharmaceutical Development: It is used in the creation of glycosylated drugs, which can enhance the bioavailability and efficacy of therapeutic agents, making treatments more effective.
  • Biotechnology: The compound plays a role in the modification of biomolecules, aiding in the design of targeted drug delivery systems that improve treatment precision.
  • Food Industry: It can be utilized in the synthesis of sweeteners and flavor compounds, contributing to the development of healthier food alternatives with reduced caloric content.
  • Material Science: This chemical is involved in the production of glycopolymers, which have applications in creating advanced materials with unique properties for various industrial uses.

Citations