151767-11-2

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

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

Downstream Products

• 617698-87-0 phenyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside 
• 885453-92-9 tigogenin 3β-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside) 
• 532983-42-9 (25R)-3β-O-[2,4-di-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranosyl]-26-O-benzoyl-β-D-glucopyranosyl-cholest-5-ene-16,22-dione 
• 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 
• 120969-06-4 diosgenyl 2,3,4,6-O-tetra-benzoyl-β-D-glucuronopyranoside 
• 14144-06-0 trillin 
• 335591-72-5 diosgenyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→4)-[2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→2)]-3,6-di-O-pivaloyl-β-D-glucopyranoside 
• 64768-19-0 4-(methoxy)phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 
• 1415639-05-2 4-(methoxycarbonyl)phenyl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside 
• 1415639-06-3 4-(methoxycarbonyl)phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

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.

Photolabile Protecting Group-Mediated Synthesis of 2-Deoxy-Glycosides

A green and efficient photolabile protecting group (PPG)-mediated glycosidation approach for the synthesis of 2-deoxy-glycosides is reported. By employing ortho-nitrobenzyl carbonate (oNBC) as PPG, N,N-dimethylformamide (DMF)-modulated SPhosAuNTf2/s

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

Gold(I)-Catalyzed Glycosylation with Glycosyl Ynenoates as Donors

A simple and versatile glycosylation method with both armed and disarmed glycosyl ynenoates as donors is developed. Employing a gold(I) complex as catalyst with or without the assistance of TfOH, the scope of the present glycosylation protocol is very wid

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.

Highly efficient synthesis and antitumor activity of monosaccharide saponins mimicking components of Chinese folk medicine Cordyceps sinensis

Ergosterol 3-O-β-d-glucopyranoside (1a) and ergosterol 3-O-d-galactopyranoside (1b) were highly efficiently synthesized and evaluated for their inhibitory activities against two tumor cell lines. The structures of these compounds were extensively confirmed by 1H, 13C NMR, IR, and HRMS. Compounds 1a and 1b exhibited interesting cytotoxic profiles. The antitumor activity of compound 1a was higher than that of 1b.

Facile synthesis of four natural triterpene saponins with important antitumor activity

The first synthesis of four natural triterpene saponins, which exhibit significant antitumor activities, was concisely achieved by adopting a stepwise glycosylation. The key intermediate 13 was afforded via Bu2SnO-mediated regioseletive benzoylation. Duri

Synthesis of betulin-3-yl ss-D-glucopyranoside

Two concise routes toward betulin-3-ylss- D-glucopyranoside, being different in the protection of primary alcohol of betulin, were developed. The synthesis adopted a stepwise glycosidation method employing glycosyl trichloroacetimidate as donor.

TRITERPENES DERIVATIVES AND USES THEREOF AS ANTITUMOR AGENTS OR ANTI-INFLAMMATORY AGENTS

A compound of formula (1): wherein R1 is selected from the group consisting of H, α-L-Rhamnopyranose, α-D-Mannopyranose, β-D-Xylopyranose, β-D-Glucopyranose, and α-D-Arabinopyranose; R2 is selected from CH3, COOH, CH2OH, COOCH3 and CH2O-α-D-Arabinopyranose; with the proviso that the compound of formula (I) is not a compound of formula (I) wherein R1 is β-D-Glucopyranose and R2 is COOH; wherein R1 is α-L-Rhamnopyranose and R2 is CH3; wherein R1 is β-D-Glucopyranose and R2 is CH2OH; wherein R1 is β-D-Xylopyranose and R2 is CH2OH; wherein R1 is α-L-Rhamnopyranose and R2 is COOCH3, wherein R1 is H and R2 is CH3; wherein R1 is H and R2 is CH2OH; wherein R1 is H and R2 is COOH; or wherein R1 is H and R2 is COOCH3, or a pharmaceutically acceptable salt thereof.

Synthetic Method of 20 (S)-Ginsenoside Rh2

A synthetic method of 20(s)-ginsenoside Rh2, that is 20(S)-protopanaxdiol-3-O-β-D-glucopyranoside, is comprised of: protecting protopanaxdiol (A1) selectively first to produce monosubstituted protopanaxdiol (A2); and Glycosidating the monosubstituted protopanaxdiol with Glucopyranosyl donor in the presence of Lewis acid catalyst; Deprotecting the product; Then separating and purifying to obtain 20(s)-ginsenoside Rh2. The method is conducted under mild condition at low cost, and affords product with high stereoselectivity, high yield and purity. Therefore, the synthetic method of the present invention is suitable for production on large scale.