16741-27-8

Basic information

• Product Name: ACETOBROMOFUCOSE
• Synonyms: ACETOBROMOFUCOSE;2,3,4-TRI-O-ACETYL-A-L-FUCOPYRANOSYL BROMIDE;2,3,4-Tri-O-acetyl-α-L-fucopyranosyl Bromide;2,3,4-Tri-O-acetyl-6-deoxy-α-L-galactopyranosyl BroMide;6-Deoxy-α-L-galactopyranosyl BroMide 2,3,4-Triacetate;a-L-Galactopyranosyl broMide, 6-deoxy-, triacetate;2,3,4-Tri-O-acetyl-6-deoxy-alpha-L-galactopyranosyl bromide
• CAS NO: 16741-27-8
• Molecular Formula: C₁₂H₁₇BrO₇
• Molecular Weight: 353.16
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 16741-27-8.mol
• Article Data: 47

Chemical Properties

• Boiling Point: 346.078°C at 760 mmHg
• Flash Point: 163.102°C
• Appearance: /
• Density: 1.46±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.498
• Solubility: Chloroform, Dichloromethane
• CAS DataBase Reference: ACETOBROMOFUCOSE(CAS DataBase Reference)
• NIST Chemistry Reference: ACETOBROMOFUCOSE(16741-27-8)
• EPA Substance Registry System: ACETOBROMOFUCOSE(16741-27-8)

Safety Data

• Hazardous Substances Data: 16741-27-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Acetobromofucose is an intermediate used in the synthesis of 2,6-Dideoxy-2-fluoro-L-galactopyranose 1,3,4-Triacetate (D440910), which is a reactant in the preparation of β-purine-diphosphate sugars (GDP-fucose-analogs)

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 
• 30571-58-5 L-fucose tetraacetate 
• 6696-41-9 alpha-L-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 
• 73-34-7 6-deoxy-L-talopyranoe 
• 7404-35-5 Acetic acid (3R,4R,5R,6S)-2,3,5-triacetoxy-6-methyl-tetrahydro-pyran-4-yl ester 
• 643-17-4 α-D-rhamnopyranose 
• 1187858-70-3 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 73-34-7 D-Fucose 
• 64-19-7 acetic acid 
• 4026-27-1 1,2:3,4-di-O-isopropylidene-α-D-fucopyranose 
• 108-24-7 acetic anhydride 
• 51921-33-6 1,2,3,4-tetra-O-acetyl-D-fucopyranose 

Downstream Products

• 34972-61-7 (4R)-4r-diethoxymethyl-5t-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-(tri-O-acetyl-α-L-6-deoxy-galactopyranosyloxy)-methyl]-oxazolidin-2-one 
• 128473-05-2 dibenzyl 2,3,4-tri-O-acetyl-β-L-fucopyranosyl phosphate 
• 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 
• 180471-90-3 8-methoxycarbonyloctyl 2,3,4-tri-O-acetyl-6-deoxy-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 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 

Relevant articles and documents

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.

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.

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.

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.