140223-15-0

Basic information

• Product Name: 1,2,3,4-Tetra-O-benzoyl-L-fucopyranose
• Synonyms: 1,2,3,4-Tetra-O-benzoyl-L-fucose;6-Deoxy-L-galactopyranose 1,2,3,4-Tetrabenzoate
• CAS NO: 140223-15-0
• Molecular Formula: C₃₄H₂₈O₉
• Molecular Weight: 580.58
• Product Categories: Carbohydrates & Derivatives
• Mol File: 140223-15-0.mol

Chemical Properties

• Appearance: /
• Stability: Store in Freezer
• CAS DataBase Reference: 1,2,3,4-Tetra-O-benzoyl-L-fucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Tetra-O-benzoyl-L-fucopyranose(140223-15-0)
• EPA Substance Registry System: 1,2,3,4-Tetra-O-benzoyl-L-fucopyranose(140223-15-0)

Safety Data

• Hazardous Substances Data: 140223-15-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,2,3,4-Tetra-O-benzoyl-L-fucopyranose is used as a synthetic intermediate for the production of various complex organic molecules. Its application is primarily due to its unique structure, which allows for selective functionalization and the formation of diverse chemical entities. The benzoyl groups can be selectively removed or modified, enabling the synthesis of a wide range of target compounds.
Used in Pharmaceutical Industry:
1,2,3,4-Tetra-O-benzoyl-L-fucopyranose is used as a building block for the development of novel pharmaceutical compounds. Its unique structure and reactivity make it an attractive candidate for the design of new drugs with potential therapeutic applications. The compound can be further modified and functionalized to create molecules with specific biological activities, such as anti-cancer, anti-inflammatory, or anti-microbial properties.
Used in Chemical Research:
1,2,3,4-Tetra-O-benzoyl-L-fucopyranose is also used as a research tool in the field of chemistry. Its unique structure and reactivity make it an interesting subject for studying various organic reactions, reaction mechanisms, and the development of new synthetic methodologies. Additionally, it can be used to investigate the properties of sugar derivatives and their interactions with other molecules, providing valuable insights into the chemistry of carbohydrates and their potential applications.

Upstream product

• 73-34-7 L-rhamnose 
• 98-88-4 benzoyl chloride 
• 6014-42-2 L-rhamnose 
• 73-34-7 6-deoxy-L-galactose 
• 2438-80-4 L-Fucose 
• 3615-41-6 L-Rhamnose 
• 6130-58-1 kaempferol-3-rutinoside 
• 1326303-82-5 4',4''',5,5'',7,7''-hexahydroxy-3,3''-O-rutinosyl-3',3'''-bisflavonoyl ether 
• 6155-35-7 L-rhamnose monohydrate 

Downstream Products

• 15356-10-2 1,1-bis-benzoylamino-1,6-dideoxy-L-mannitol 
• 73068-86-7 p-tolyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 
• 15839-70-0 guanosine-5'-diphospho-β-L-fucose 
• 30174-43-7 UDP-β-L-fucose 
• 1218904-51-8 2,3,4-tri-O-benzoyl-α-L-fucopyranosyl iodide 
• 340964-54-7 allyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->6)-3,4-di-O-benzoyl-α-D-glucopyranoside 
• 161007-95-0 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 
• 862108-13-2 2,3,4-tri-O-benzoyl-α-L-rhamnopyranose 
• 511548-70-2 tri-O-benzoyl-α-L-rhamnopyranosyl iodide 

Relevant articles and documents

Boronic acid-catalyzed final-stage site-selective acylation for the total syntheses of O-3′-acyl bisabolol β-D-fucopyranoside natural products and their analogues

The first concise total syntheses of O-3′-senecioyl α-bisabolol β-D-fucopyranoside (4a) and O-3′isovaleroyl α-bisabolol β-D-fucopyranoside (4b) were achieved through final-stage site-selective acylation via the activation of cis-vicinal diols by imidazole

Suppression of cytokine production by newly isolated flavonoids from pepper

New flavonoid glycoside, kaempferol 3-O-α-[(6-P-coumaroyl galactopyranosyl-O-β-(→4)-O-α-rhamnopyranosyl-(1→4)]-O-α-rhamnopyranoside 1, in addition to five known flavonoid glycosides (2–6) kaempferol 3-O-[α-rhamnopyranosyl-(1→4)-O-α-rhamnopyranosyl-(1→6)-O]-β-galactopyranoside (kaempferol 3-O-β-isorhamninoside) 2, quercetin 3-O-[(2,3,4-triacetyl-α-rhamnopyranosyl)-(1 → 6)-β-galactopyranoside 3, quercetin 3-O-[(2,4-diacetyl-α-rhamnopyranosyl)-(1 → 6)]-3,4-diacetyl-β-galactopyranoside 4, quercetin 3-O-[(2,4-diacetyl-α-rhamnopyranosyl)-(1→6)]-2,4-diacetyl-β-galactopyranoside 5, quercetin 3-O-[(2,3,4-triacetyl-α-rhamnopyranosyl)-(1 → 6)-3-acetyl-β-galactopyranoside 6 were isolated from bell pepper (Capsicum annum L.) fruits and tested for both anti-inflammatory activity through cytokine production (TNF-α and IL-1β) and antioxidant activity through scavenging effect on 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Compounds 1–3 significantly suppressed production of TNF-α / IL-1β in cultured THP-1 cells previously co-stimulated by LPS in a dose-dependent manner (10.2/49.1, 28.1/55.7, and 35.2/57.5 μM respectively) whereas compounds 4–6 have relatively weaker inhibitory activity. (45.3/73.5, 48.2/65.6, and 42.2/67.4 μM respectively). All compounds 1–6 showed no cytotoxic activity against the growth of THP-1where the percentage of cell viability was (127.4, 108.5, 105.4, 103.9, 103.4, and 104.2 μM respectively). All isolated compounds exhibited higher radical scavenging activity than ascorbic acid in (DPPH) assay. These results indicated that bell pepper fruits could be an effective candidate for ameliorating inflammatory-associated complications.

Sterically Hindered 2,4,6-Tri- tert-butylpyridinium Salts as Single Hydrogen Bond Donors for Highly Stereoselective Glycosylation Reactions of Glycals

We demonstrate here that the strained and bulky protonated 2,4,6-tri-tert-butylpyridine salts serve as efficient catalysts for highly stereoselective glycosylations of various glycals. Moreover, the mechanism of action involves an interesting single hydrogen bond mediated protonation of glycals and not via the generally conceived Br?nsted acid pathway. The counteranions also play a role in the outcome of the reaction.

Visible Light Enables Aerobic Iodine Catalyzed Glycosylation

A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.

BIARYL AMIDES WITH MODIFIED SUGAR GROUPS FOR TREATMENT OF DISEASES ASSOCIATED WITH HEAT SHOCK PROTEIN PATHWAY

Provided are biaryl amides and coumarin-based compounds with modified sugar groups for treatment of diseases associated with heat shock protein pathway. The compounds having the following formulas, wherein variables are as defined herein. Formulae (I), (II), (III), (IV), and (V), Pharmaceutical compositions of the compounds are also provided. These biaryl amides and coumarin-based derivatives with modified sugar groups are useful for treatment and prevention of diseases and disorders, including neurological disorders, such as neurodegenerative diseases and nerve damaging disorders, for example, diabetic peripheral neuropathy.

Senescence tracers

The instant invention relates to novel compounds useful for visualizing cell senescence, their preparation and use. In particular, this invention relates to novel fucose and amino-quinoline derivatives useful as senescence traces and their preparation.

Isoquinoline-1-Carboxylate as a Traceless Leaving Group for Chelation-Assisted Glycosylation under Mild and Neutral Reaction Conditions

Glycosyl isoquinoline-1-carboxylate was developed as a novel benchtop stable and readily available glycosyl donor. The glycosylation reaction was promoted by the inexpensive Cu(OTf)2 salt under mild reaction conditions. The copper isoquinoline-1-carboxylate salt was precipitated from the solution and thus rendered a traceless leaving group. Surprisingly, the proton from the acceptor was absorbed by the precipitated metal complex and the reaction mixture remained at neutral pH. The copper-promoted glycosylation was also proven to be completely orthogonal to the gold-promoted glycosylation, and an iterative synthesis of oligosaccharides from benchtop stable anomeric ester building blocks becomes possible under mild reaction conditions.

Stereoselective Epimerizations of Glycosyl Thiols

Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective β-d-manno- and β-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.

Practical synthesis of latent disarmed S-2-(2-propylthio)benzyl glycosides for interrupted Pummerer reaction mediated glycosylation

Practical synthetic methods to latent disarmed S-2-(2-propylthio)benzyl (SPTB) glycosides for interrupted Pummerer reaction mediated glycosylation have been discovered. Among them, both coupling reaction of PTB-Cl with glycosyl thiols and BF3·OEt2 promoted reaction of peracylated glycosides with PTB-SH produced peracylated SPTB glycosides in large scales and with high efficiency.

Two new P-coumaroyl flavonoid glycosides having Cytokine increasing activity from Centaurium spicatum L

Two new P-coumaroyl flavonol glycosides, Kaempferol 3-O-[β-D-glucopyranosyl- (1?→?4)-α-L-rhamnopyranosyl-(1?→?4)-α-L-rhamnopyranosyl-(1?→?6)-(4 trans- P-coumaroyl)]-β-D- galactopyranoside (1) and Quercetin 3-O-[β-D-glucopyranosyl-(1?→?4)-α-L-rhamnopyranos