151767-11-2

Basic information

• Product Name: 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate
• Synonyms: 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate
• CAS NO: 151767-11-2
• Molecular Weight: 740.978
• Mol File: 151767-11-2.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate(151767-11-2)
• EPA Substance Registry System: 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate(151767-11-2)

Safety Data

• Hazardous Substances Data: 151767-11-2(Hazardous Substances Data)

Usage

Chemical structure

A derivative of glucose with four benzoyl groups (2,3,4,5-tetra-O-benzoyl) and a trichloroacetimidate moiety attached.

Type of compound

A chemical compound used as a glycosyl donor in organic synthesis.

Usage

Commonly utilized in the formation of glycosidic bonds in the synthesis of complex carbohydrate molecules.

Reactivity

High reactivity towards a variety of hydroxyl-containing compounds, allowing for efficient and selective glycosylation reactions.

Leaving group

The trichloroacetimidate moiety serves as a leaving group in glycosylation reactions, facilitating the formation of the glycosidic bond.

Versatility

Widely used in the field of carbohydrate chemistry for the synthesis of diverse natural and synthetic compounds.

Upstream product

• 2280-44-6 D-Glucose 
• 98-88-4 benzoyl chloride 
• 165877-99-6 2,3,4,6-tetra-O-Bz-β-D-glucopyranosyl bromide 
• 22415-91-4 1,2,3,4,6-penta-O-benzoyl-α-D-glucopyranose 
• 545-06-2 trichloroacetonitrile 
• 627466-64-2 2,3,4,6-tetra-O-benzoyl-D-glucopyranose 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside 

Downstream Products

• 1354766-16-7 ergosterol-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside) 
• 130155-33-8 (3β,22E)-ergosta-5,7,22-trien-3-yl D-glucopyranoside 

Relevant articles and documents

GLUCOSE TRIPTOLIDE CONJUGATES AND USES THEREOF

A major hurdle in the treatment of cancer is chemoresistance induced under hypoxia that is characteristic of tumor microenvironment. Triptolide, a potent inhibitor of eukaryotic transcription, possesses potent antitumor activity. However, its clinical potential has been limited by toxicity and water solubility. To address those limitations of triptolide, the present disclosure designed and synthesized glucose-triptolide conjugates (glutriptolides) and demonstrated their antitumor activity in vitro and in vivo. The glutriptolides disclosed herein possess improved stability in human serum, greater selectivity towards cancer over normal cells and increased potency against cancer cells. Importantly, the glutriptolides are more potent against cancer cells under hypoxic conditions in contrast to existing cytotoxic drugs. These glutriptolides also exhibit sustained antitumor activity, prolonging survival in a prostate cancer metastasis animal model. Together, these findings suggest a new strategy to overcome chemoresistance through conjugation of cytotoxic agents to glucose.

Gold(I)-Catalyzed Intermolecular Rearrangement Reaction of Glycosyl Alkynoic β-Ketoesters for the Synthesis of 4- O-Glycosylated 2-Pyrones

A new gold(I)-catalyzed rearrangement reaction with glycosyl alkynoic β-ketoesters as substrates is developed. The rearrangement reactions under the catalysis of PPh3AuOTf proceeded smoothly to afford a range of 4-O-glycosylated 2-pyrones. Base

Synthesis of a chlorogenin glycoside library using an orthogonal protecting group strategy

Naturally occurring spirostanol saponins bear a chacotriose, α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→4)] -β-d-glucopyranose residue as the oligosaccharide moiety which is believed to be important for biological activity. Herein the development of a concise, combinatorial method for the synthesis of two series of glycan variants at the 2′ and/or 4′ positions of chacotriose is described and the structure-activity relationships of the glycone part at 3-OH of chlorogenin investigated. These compounds were found to be weakly-cytotoxic toward leukemia cell lines CCRF and HL-20, indicating that the chacotriose moiety is important for anticancer activity.