34819-86-8

Basic information

• Product Name: 3,4-DI-O-ACETYL-6-DEOXY-L-GLUCAL
• Synonyms: 3,4-DI-O-ACETYL-6-DEOXY-L-GLUCAL, 98% MIN., HPLC;1,5-Anhydro-2,6-dideoxy-L-arabino-Hex-1-enitol 3,4-Diacetate;6-Deoxy-L-glucal Diacetate;Diacetyl-L-rhamnal;L-Rhamnal Diacetate;(2S)-2,3-Dihydro-2β-methyl-4H-pyran-3α,4β-diol diacetate;(2S)-2β-Methyl-3α,4β-diacetoxy-3,4-dihydro-2H-pyran;(4S)-4α,5β-Diacetoxy-6α-methyl-5,6-dihydro-4H-pyran
• CAS NO: 34819-86-8
• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.22
• EINECS: 252-228-7
• Product Categories: 13C & 2H Sugars;Biochemistry;Glucose;Glycals;Sugars;Carbohydrates & Derivatives;Intermediates
• Mol File: 34819-86-8.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 68-69 °C0.06 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colorless to Yellow/Viscous Liquid
• Density: 1.116 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00149mmHg at 25°C
• Refractive Index: n20/D 1.454(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Dichloromethane
• BRN: 84954
• CAS DataBase Reference: 3,4-DI-O-ACETYL-6-DEOXY-L-GLUCAL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DI-O-ACETYL-6-DEOXY-L-GLUCAL(34819-86-8)
• EPA Substance Registry System: 3,4-DI-O-ACETYL-6-DEOXY-L-GLUCAL(34819-86-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 34819-86-8(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

A DNA-binding agent.

InChI:InChI=1/C10H14O5/c1-6-10(15-8(3)12)9(4-5-13-6)14-7(2)11/h4-6,9-10H,1-3H3/t6-,9-,10-/m0/s1

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 116050-47-6 Acetic acid (2S,3S,4S)-3-acetoxy-2-methyl-6-(pyridin-2-ylsulfanyl)-tetrahydro-pyran-4-yl ester 
• 14133-63-2 methyl 2,3-O-isopropylidene-α-L-rhamnoside 
• 6014-42-2 L-rhamnose 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 53657-42-4 L-rhamnal 
• 883884-80-8 1,2,3,4-tetra-O-acetyl-L-rhamnose 
• 73-34-7 6-deoxy-L-glucose 
• 30021-94-4 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 
• 69980-52-5 2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide 
• 3615-41-6 L-Rhamnose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 73-34-7 L-rhamnose 

Downstream Products

• 95666-88-9 Acetic acid (2S,3R,6S)-2-methyl-6-(2-methyl-cyclohex-2-enyl)-3,6-dihydro-2H-pyran-3-yl ester 
• 95666-88-9 Acetic acid (2S,3R,6R)-2-methyl-6-(2-methyl-cyclohex-2-enyl)-3,6-dihydro-2H-pyran-3-yl ester 
• 83241-05-8 (6S)-(6-methyltetrahydropyran-2-yl)acetophenone 
• 115093-66-8 α-1-(4'-acetoxy-2',3',6'-trideoxy-D-threo-hex-2'-enopyranosyl)acetophenone 
• 115093-65-7 1-((4-O-acetyloxy-5-methyl)-2,3,6-trideoxy-β-L-erythro-hex-2-enopyranosyl)-1-phenylethanone 
• 148163-95-5 methyl 3,4-di-O-benzyl-2-O-(3,4-di-O-acetyl-2-deoxy-2-iodo-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 95667-10-0 Acetic acid (2S,3R,6R)-6-(4-tert-butyl-cyclohex-1-enylmethyl)-2-methyl-3,6-dihydro-2H-pyran-3-yl ester 
• 95667-10-0 Acetic acid (2S,3R,6S)-6-(4-tert-butyl-cyclohex-1-enylmethyl)-2-methyl-3,6-dihydro-2H-pyran-3-yl ester 
• 95667-10-0 Acetic acid (2S,6R)-6-(4-tert-butyl-cyclohex-1-enylmethyl)-2-methyl-3,6-dihydro-2H-pyran-3-yl ester 
• 95667-10-0 Acetic acid (2S,6S)-6-(4-tert-butyl-cyclohex-1-enylmethyl)-2-methyl-3,6-dihydro-2H-pyran-3-yl ester 
• 89912-77-6 7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-mannopyranosyl)daunomycinone 
• 190060-81-2 7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-β-L-glucopyranosyl)daunomycinone 
• 95645-16-2 Benzoic acid 3-((2S,5R,6S)-5-acetoxy-6-methyl-5,6-dihydro-2H-pyran-2-ylmethyl)-but-3-enyl ester 
• 89912-77-6 7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-β-L-glucopyranosyl)daunomycinone 

Relevant articles and documents

Synthetic routes toward pentasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O181

An efficient synthetic strategy has been developed for the synthesis of the pentasaccharide repeating unit corresponding to the O-antigen of Escherichia coli O181. A one-pot, two step iterative glycosylation and [2 + 3] block glycosylation strategy have been adopted for the construction of the pentasaccharide derivative 2, which was then transformed into target compound 1 after a series of functional group transformations. Here H2SO4-silica has been used successfully as a promoter for all glycosylation reaction. The stereoselective outcomes of all glycosylation reactions were very good. The 2-acetamido-2,6-dideoxy-L-glucose (L-QuipNAc) building block was obtained from known carbohydrate L-rhamnose precursors.

An expeditious stereoselective synthesis of natural (-)-Cassine via cascade HWE [3 + 2]-cycloaddition process

l-Rhamnose is transformed to (-)-Cassine via a remarkable four step one pot reaction. The Horner-Wadsworth-Emmons [3 + 2]-1,3-dipolar cycloaddition reaction cascade is the pivotal step in this reaction sequence and makes the synthesis highly efficient. The Royal Society of Chemistry 2006.

Chaunopyran A: Co-Cultivation of Marine Mollusk-Derived Fungi Activates a Rare Class of 2-Alkenyl-Tetrahydropyran

Co-cultivation of Chaunopycnis sp. (CMB-MF028) and Trichoderma hamatum (CMB-MF030), fungal strains co-isolated from the inner tissue of an intertidal rock platform mollusc (Siphonaria sp), resulted in transcriptional activation of a rare class of 2-alkenyl-tetrahydropyran, chaunopyran A (7), and biotransformation and deactivation of the antifungal pyridoxatin (1), to methyl-pyridoxatin (8). This study illustrates the complexity of offensive and counter-offensive molecular defenses encountered during fungal co-cultivation, and the opportunities for activating new, otherwise transcriptionally silent secondary metabolites.

Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.

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.