16741-27-8

Usage

Uses

Used in Pharmaceutical Industry:
ACETOBROMOFUCOSE is used as a key intermediate for the synthesis of 2,6-Dideoxy-2-fluoro-L-galactopyranose 1,3,4-Triacetate (D440910). ACETOBROMOFUCOSE is essential in the preparation of β-purine-diphosphate sugars (GDP-fucose-analogs), which have potential applications in the development of new drugs and therapies for various medical conditions. The use of ACETOBROMOFUCOSE in this process highlights its importance in the pharmaceutical industry, as it contributes to the creation of innovative and effective treatments.

InChI:InChI=1/C12H17BrO7/c1-5-9(18-6(2)14)10(19-7(3)15)11(12(13)17-5)20-8(4)16/h5,9-12H,1-4H3/t5?,9-,10+,11+,12-/m1/s1

Upstream product

• 84635-54-1 methyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside 
• 64913-16-2 L-fucose tetraacetate 
• 30571-58-5 L-fucose tetraacetate 
• 73-34-7 6-deoxy-L-galactose 
• 108-24-7 acetic anhydride 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-6-deoxy-α-D-galactopyranose 
• 73-34-7 D-Fucose 
• 34371-41-0 1,2,3,4-tetra-O-acetyl-6-deoxy-β-D-galactopyranose 
• 28161-52-6 (2R,3R,4S,5R,6R)-6-Methyl-tetrahydro-pyran-2,3,4,5-tetraol 
• 7404-35-5 Acetic acid (3R,4R,5R,6S)-2,3,5-triacetoxy-6-methyl-tetrahydro-pyran-4-yl ester 
• 73-34-7 6-deoxy-L-talopyranoe 
• 643-17-4 α-D-rhamnopyranose 
• 1187858-70-3 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 64-19-7 acetic acid 

Downstream Products

• 205252-13-7 (S)-4-Benzyloxycarbonylamino-4-[6-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexylcarbamoyl]-butyric acid methyl ester 
• 205252-97-7 (S)-4-(6-Acetoxy-hexylcarbamoyl)-4-benzyloxycarbonylamino-butyric acid methyl ester 
• 95581-07-0 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-L-fucopyranose 
• 128473-05-2 dibenzyl 2,3,4-tri-O-acetyl-β-L-fucopyranosyl phosphate 
• 296776-04-0 4-methylumbelliferyl 6'-O-(tert-butyldiphenylsilyl)-3'-O-(2'',3'',4''-tri-O-acetyl-α-L-fucopyranosyl)-β-D-galactopyranoside 
• 224964-33-4 allyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 167612-34-2 phenyl 6-deoxy-2,3,4-tri-O-acetyl-1-thio-β-L-galactopyranoside 

Relevant academic research and scientific papers

Azidonitration of di-O-acetyl-L-fucal: X-Ray crystal structures of intermediate azidodeoxysugars and of the bacterial aminosugar N-acetyl-L-fucosamine

The azidonitration of di-O-acetyl-L-fucal has previously been shown to be an efficient route to the bacterial aminosugar N-acetyl-L-fucosamine. Upon repeating this sequence, with updated versions of the glycal formation and amide installation steps, we have obtained X-ray crystal structures of several of the addition products, which are now reported along with the solid-state structure of N-acetyl-L-fucosamine itself. Copyright Taylor & Francis Group, LLC.

Alpha-L-fucosidase detection probe and preparation method and application thereof

The invention discloses an alpha-L-fucosidase detection probe. The structural general formula of the probe is shown in the specification, wherein in the formula I, R1 is an acetyl-protected monosaccharidyl or monosaccharidyl group; and R2 is a pyranonitrile group or a benzopyran nitrile group. The alpha-L-fucosidase detection probe prepared by the invention improves the detection sensitivity, can detect serum AFU with high selectivity, and can be used for kits or drugs for positioning and detecting cancer cells.

Excited-State Palladium-Catalyzed 1,2-Spin-Center Shift Enables Selective C-2 Reduction, Deuteration, and Iodination of Carbohydrates

Excited-state catalysis, a process that involves one or more excited catalytic species, has emerged as a powerful tool in organic synthesis because it allows access to the excited-state reaction landscape for the discovery of novel chemical reactivity. Herein, we report the first excited-state palladium-catalyzed 1,2-spin-center shift reaction that enables site-selective functionalization of carbohydrates. The strategy features mild reaction conditions with high levels of regio- and stereoselectivity that tolerate a wide range of functional groups and complex molecular architectures. Mechanistic studies suggest a radical mechanism involving the formation of hybrid palladium species that undergoes a 1,2-spin-center shift followed by the reduction, deuteration, and iodination to afford functionalized 2-deoxy sugars. The new reactivity will provide a general approach for the rapid generation of natural and unnatural carbohydrates.

Nickel-Catalyzed Radical Migratory Coupling Enables C-2 Arylation of Carbohydrates

Nickel catalysis offers exciting opportunities to address unmet challenges in organic synthesis. Herein we report the first nickel-catalyzed radical migratory cross-coupling reaction for the direct preparation of 2-Aryl-2-deoxyglycosides from readily available 1-bromosugars and arylboronic acids. The reaction features a broad substrate scope and tolerates a wide range of functional groups and complex molecular architectures. Preliminary experimental and computational studies suggest a concerted 1,2-Acyloxy rearrangement via a cyclic five-membered-ring transition state followed by nickel-catalyzed carbon-carbon bond formation. The novel reactivity provides an efficient route to valuable C-2-Arylated carbohydrate mimics and building blocks, allows for new strategic bond disconnections, and expands the reactivity profile of nickel catalysis.

Halogenation and anomerization of glycopyranoside by TESH/bromine and BHQ/bromine

Treatment of peracetylated glycosides and β-isopropyl glycosides with halogen in the presence of TESH and BHQ has been found to result in the halogenation and the anomerization, respectively. Peracetylatedglycosides treaded with I2/TESH or Br2/TESH leading tothe formation of corresponding glycosyl halides, and b-isopropyl glycosidesreacted with Br2/BHQ resulting in the formation of a-glycosides. The anomerizationof glycosidic bond was considered to be catalyzed by in situ formation of hydrogenbromide from the mixing of Br2/BHQ.

Neuroprotective activity of different monosaccharide-modified gastrodin analogs

Gastrodin is a very important and well-known bioactive glycoside compound in Chinese medicine. It is also known as a drug with neuroprotective function. Here, a practical diversified synthesis of a series of gastrodin analogs was reported, which involved four-step procedures consisting of bromination, oxidation, etherification, and reduction. Various gastrodin analogs were obtained in good yields. The compound 4c in this study has a good neuroprotective function: it can significantly downregulate tumor necrosis factor-α and inducible nitric oxide synthase protein levels. The results of this study can provide a research basis for the development of neuroprotective drugs.

Synthesis and cytotoxicity evaluation of glycosidic derivatives of lawsone against breast cancer cell lines

Breast cancer is the most incident and mortal cancer type in women, with an estimated 2 million new cases expected by 2020 worldwide, with 600,000 deaths. As not all breast cancer types respond to the anti-hormonal therapy, the development of new antineoplastic drugs is necessary. Lawsone (2-hydroxy-1,4-naphtoquinone) is a natural bioactive naphtoquinone displaying a range of activities, with dozens of derivatives described in the literature, including some glycosides possessing antitumor activity. Here, a series of glycosides of lawsone are reported for the first time and all compounds displayed good activity against the SKBR-3 cell line, with IC50 below 10 μM. The most promising derivative was the glycosyl triazole derived from peracetylated D-glucose (11), which showed better cytotoxicity against SKBR-3 (IC50 = 0.78 μM), being the most selective toward this tumoral cell (SI > 20). All compounds described in this work were more active than lawsone, indicating the importance of the carbohydrate and glycosyl triazole moiety for activity.

Lewis acid promoted anomerisation of alkyl O- and S-xylo-, arabino- and fucopyranosides

Pentopyranoside and 6-deoxyhexopyranosides, such as those from D-xylose, L-arabinose and L-fucose are components of natural products, oligosaccharides or polysaccharides. Lewis acid promoted anomerisation of some of their alkyl O- and S-glycopyranosides i

Total Syntheses of Resin Glycosides Murucoidins IV and v

Murucoidins IV and V, two bioactive resin glycosides with complex yet similar structures isolated from the morning glory family, were synthesized in a convergent manner. All of the glycosylations in these syntheses including the key [3 + 2] coupling were

OLIGONUCLEOTIDE DERIVATIVE, OLIGONUCLEOTIDE CONSTRUCT USING THE SAME, AND METHODS FOR PRODUCING THEM

The oligonucleotide derivative of the present invention is represented by Formula (1). This derivative is considered to be introduced into cells by binding of its amino sugar chain moiety to a ligand on cell surfaces, and have selective drug delivery function. The oligonucleotide derivative can be easily synthesized and introduced into cells without using a lipofection reagent. wherein—A and B are independently modified or unmodified oligonucleotides whose total chain length is 3 or more, and A and B do not contain hydroxyl groups at 3′ and 5′ ends of the oligonucleotide; S represents a sugar substituent, a peptide chain, or a tocopherol-binding group; and an alkyl group may be bound instead of hydrogen bound to a benzene ring.