5158-64-5

Basic information

• Product Name: 2,3,4-TRI-O-ACETYL-ALPHA-L-RHAMNOPYRANOSYL BROMIDE
• Synonyms: 2-O,3-O,4-O-Triacetyl-α-L-rhamnopyranosyl bromide;6-Deoxy-α-L-mannopyranosyl bromide triacetate;Tri-O-acetyl-α-rhamnopyranosyl bromide;2,3,4-TRI-O-ACETYL-α-L-RHAMNOPYRANOSYL BROMIDE;ACETOBROMO-ALPHA-L-RHAMNOSE;2,3,4-TRI-O-ACETYL-ALPHA-L-RHAMNOPYRANOSYL BROMIDE;.alpha.-L-Mannopyranosyl bromide, 6-deoxy-, triacetate;1-Bromo-1-deoxy-α-L-rhamnopyranose 2,3,4-triacetate
• CAS NO: 5158-64-5
• Molecular Formula: C₁₂H₁₇BrO₇
• Molecular Weight: 353.16
• Mol File: 5158-64-5.mol

Chemical Properties

• Melting Point: 71-72 °C
• Boiling Point: 346.1±42.0 °C(Predicted)
• Appearance: /
• Density: 1.46±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2,3,4-TRI-O-ACETYL-ALPHA-L-RHAMNOPYRANOSYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-TRI-O-ACETYL-ALPHA-L-RHAMNOPYRANOSYL BROMIDE(5158-64-5)
• EPA Substance Registry System: 2,3,4-TRI-O-ACETYL-ALPHA-L-RHAMNOPYRANOSYL BROMIDE(5158-64-5)

Safety Data

• Hazardous Substances Data: 5158-64-5(Hazardous Substances Data)

Usage

Molecular weight

412.2

Structure

A rhamnopyranose sugar ring with three acetyl groups (acetates) attached to the 2, 3, and 4 positions and a bromide group attached to the 1 position.

Derivative of rhamnose

A naturally occurring sugar found in plants and fruits.

Common use

In the synthesis of carbohydrates and glycosides.

Acetylated form

Provides greater stability and ease of manipulation in chemical reactions.

Bromide group

Adds reactivity and versatility to the molecule.

Applications

Organic synthesis and drug discovery.

Upstream product

• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 27821-10-9 1,2,3,4-tetra-O-acetate-β-L-rhamnopyranoside 
• 73-34-7 L-rhamnose 
• 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 
• 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 
• 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 
• 51921-33-6 1,2,3,4-tetra-O-acetyl-D-fucopyranose 
• 1026722-79-1 6-deoxy-L-ribo-hexulose 

Downstream Products

• 80832-18-4 benzyl 2,3,6-tri-O-benzyl-4-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-galactopyranoside 
• 73223-28-6 benzyl 3,4-di-O-benzyl-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 72384-19-1 benzyl 2,4-di-O-benzyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 118246-06-3 methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside 
• 80832-15-1 benzyl 3-O-benzoyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-galactopyranoside 
• 71348-35-1 methyl 2,4-di-O-benzyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 71348-34-0 methyl 3,4-di-O-benzyl-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 129031-02-3 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnbopyranosyl)-β-D-galactopyranoside 
• 88337-87-5 methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 
• 126990-50-9 Allyl O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-<2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->6)>-3-O-benzyl-α-D-glucopyranoside 
• 130999-26-7 4'-7-di-O-benzylquercet-3-yl 2,3,4-tri-O-acetyl-α-L-rhamnopranoside 
• 130999-27-8 4'-7-di-O-benzylquercet-3-yl 2,3,4-tri-O-acetyl-β-L-rhamnopranoside 
• 110082-84-3 Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-[2-(3,4-dimethoxy-phenyl)-ethoxy]-4-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 
• 129230-44-0 methyl 2-O-allyl-4,6-di-O-benzyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-mannopyranoside 

Relevant articles and documents

Clarifying the structure of granadaene: Total synthesis of related analogue [2]-granadaene and confirmation of its absolute stereochemistry

Streptococcus agalactiae is an important agent in the infection of neonates in the first world. One of the most extended methods for its identification is based on the detection of a characteristic red pigment in the patient samples, named [12]-granadaene (1). In this article, we present a modular and flexible approach to simple analogues of this ornithine rhamno-polyene 1 and the elucidation of the most important features of its structure: the absolute configuration at C-27, the stereochemistry of the anomeric center and the link of the amino acid ornithine to the rest of the structure.

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.

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

Tuning the Chemoselectivity of Silyl Protected Rhamnals by Temperature and Br?nsted Acidity: Kinetically Controlled 1,2-Addition vs Thermodynamically Controlled Ferrier Rearrangement

An acidity- and temperature-dependent chemoselective glycosylation of silyl-protected rhamnals with alcohols has been revealed. The reaction undergoes a 1,2-addition pathway with (±)-CSA as the catalyst at rt, affording kinetically controlled 2-deoxyl rhamnosides. In contrast, only thermodynamically controlled 2,3-unsaturated rhamnosides are formed via Ferrier rearrangement when elevating reaction temperature to 85 °C or using CF3SO3H instead. This tunable glycosylation allows facile and practical access to both 2-deoxyl and 2,3-unsaturated rhamnosides with excellent yields and high α-stereoselectivity.

Efficient synthesis of a 6-deoxy-talose containing tetrasccharide found in Franconibacter helveticus LMG23732T

Synthesis of the 6-deoxy-talose (6-dTal) containing tetrasaccharide, naturally found in Franconibacter helveticus LMG23732T, has been described. The synthetic method utilized an allyloxyethylidene group for protecting the 1-OH and 2-OH groups of rhamnopyranose and a redox reaction for synthesizing 6-deoxy talose, which eventually formed a disaccharide containing α-Glcp-(1→2)-6dTalp configured glycosidic bonds using a [2 + 2] synthetic strategy.

Photocaged Carbohydrates: Versatile Tools for Controlling Gene Expression by Light

The control of biological processes plays a central role in life science, especially the tight regulation of gene expression for biotechnological systems. In this context, optogenetic tools have emerged as an important instrument for controlling gene expression by light with high spatiotemporal resolution in a non-invasive way. Here, we present the syntheses and characterization of biofunctional photocaged carbohydrates, on the basis of the biologically most relevant carbohydrates glucose, galactose, rhamnose, and lactose. The single-step cleavage of these compounds allows both, to rapidly activate and temporary or permanently repress the transcription in E. coli after short UV-A light exposure. This study thus presents a versatile toolbox of photocaged carbohydrates for the light-triggered regulation and control of cellular processes useful for synthetic bio(techno)logy applications.

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.

Organoboron-Promoted Regioselective Glycosylations in the Synthesis of a Saponin-Derived Pentasaccharide from Spergularia ramosa

Organoboron-mediated regioselective glycosylations were employed as key steps in the total synthesis of a branched pentasaccharide from a saponin natural product. The ability to use organoboron activation to differentiate OH groups in an unprotected glycosyl acceptor, followed by substrate-controlled reactions of the obtained disaccharide, enabled a streamlining of the synthesis relative to a protective group-based approach. This study revealed a matching/mismatching effect of the relative configuration of donor and acceptor on the efficiency of a regioselective glycosylation reaction, a problem that was solved through the development of a novel boronic acid-amine copromoter system for glycosyl acceptor activation.

A short route for large-scale synthesis of per-O-acetylated C-1 Hydroxyglycopyranose

A short route for large scale synthesis of C-1 hydroxypyranose was developed starting from L-rhamnose and D-mannose. The selective hydrolysis at anomeric carbon was carried out in the presence of catalytic amount of zinc. In the current paper, X-ray crystallographic studies of 2,3,4-tri-O-acetyl-α-L-rhamnopyranose was also exploited, which crystallizes in tetragonal space group I4 along with three water molecules in asymmetric unit.