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

• 64913-16-2 L-fucose tetraacetate 
• 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 
• 28161-52-6 (2R,3R,4S,5R,6R)-6-Methyl-tetrahydro-pyran-2,3,4,5-tetraol 
• 34371-41-0 1,2,3,4-tetra-O-acetyl-6-deoxy-β-D-galactopyranose 
• 108-24-7 acetic anhydride 
• 51921-33-6 1,2,3,4-tetra-O-acetyl-D-fucopyranose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-6-deoxy-α-D-galactopyranose 
• 6696-41-9 alpha-L-fucose 

Downstream Products

• 88819-10-7 benzyl 6-deoxy-3,4-O-isopropylidene-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside 
• 128473-05-2 dibenzyl 2,3,4-tri-O-acetyl-β-L-fucopyranosyl phosphate 
• 482648-35-1 phenylmethyl 2,3,4-triacetyl-β-D-fucopyranoside 
• 441775-34-4 Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-methyl-tetrahydro-pyran-4-yl ester 
• 373606-28-1 dibutyl 2-O-benzyl-3,4-di-O-pivaloyl-β-L-fucopyranoside phosphate 
• 373606-55-4 2-O-benzyl-3,4-di-O-pivaloyl-α-L-fucopyranosyl trichloroacetimidate 
• 373606-48-5 2,2-Dimethyl-propionic acid (2S,3S,4R,5R,6S)-3-benzyloxy-5-(2,2-dimethyl-propionyloxy)-6-methyl-2-pent-4-enyloxy-tetrahydro-pyran-4-yl ester 
• 373606-47-4 (3aR,4S,6S,7S,7aR)-7-Benzyloxy-2,2,4-trimethyl-6-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 405218-92-0 (2-azido-3,4-di-O-acetyl-2-deoxy-β-D-fucopyranosyl) dibenzyl phosphate 
• 405218-93-1 (2-azido-3,4-di-O-acetyl-2-deoxy-α-D-fucopyranosyl) dibenzyl phosphate 
• 578738-08-6 phenyl 2,6-di-O-benzoyl-4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-3-O-[3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl]-1-thio-β-D-glucopyranoside 
• 578738-09-7 allyl 2,6-di-O-benzoyl-4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-3-O-[3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl]-β-D-glucopyranoside 
• 578738-14-4 C₅₇H₆₂O₂₀ 
• 196397-63-4 phenyl 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 

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.

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.

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.