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
• Article Data: 40

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 
• 6014-42-2 L-rhamnose 
• 108-24-7 acetic anhydride 
• 73-34-7 L-rhamnose 
• 30021-94-4 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 
• 1026722-79-1 6-deoxy-L-ribo-hexulose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-6-deoxy-α-D-galactopyranose 
• 51921-33-6 1,2,3,4-tetra-O-acetyl-D-fucopyranose 
• 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 
• 4026-27-1 1,2:3,4-di-O-isopropylidene-α-D-fucopyranose 
• 64-19-7 acetic acid 

Downstream Products

• 73351-09-4 menthyl-rhamnopyranoside 
• 508-75-8 convallatoxin 
• 93414-06-3 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-α-D-galactopyranoside 
• 77667-38-0 3-hydroxy-2-nitrophenyl 2,3,4-tri-O-acetyl-β-D-fucopyranoside 
• 84729-97-5 p-nitrophenyl 2,3,4-tri-O-acetyl-β-D-fucopyranoside 
• 144685-23-4 methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,4-tri-O-acetyl-6-deoxy-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 27894-28-6 Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(6-benzoylamino-purin-9-yl)-6-methyl-tetrahydro-pyran-3-yl ester 
• 88819-10-7 benzyl 6-deoxy-3,4-O-isopropylidene-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside 
• 88819-15-2 benzyl 3,4-di-O-benzyl-6-deoxy-2-O-(α-L-rhamnopyranosyl)-α-L-talopyranoside 
• 3359-36-2 benzyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranoside 
• 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 

Relevant articles and documents

The C-32 triacetyl-L-rhamnose derivative of ascomycin: A potent, orally active macrolactone immunosuppressant

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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.

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.