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 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 
• 5160-09-8 2,3,4‐tri‐O‐acetyl-α-L‐rhamnopyranosyl chloride 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 19185-89-8 2-methyl-2,3-dihydro-4H-pyran-4-one 
• 108-24-7 acetic anhydride 
• 68673-59-6 Acetic acid 2-methyl-4-oxo-3,4-dihydro-2H-pyran-3-yl ester 
• 95475-50-6 4-O-acetyl-L-rhamnal 
• 115888-74-9 3,4-di-O-acetyl-L-rhamnal 
• 7658-08-4 D-quionovose 
• 2438-80-4 L-Fucose 
• 6014-42-2 L-rhamnose 
• 64-19-7 acetic acid 

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.

Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks

An automated continuous flow system capable of producing protected deoxy-sugar donors from commercial material is described. Four 2,6-dideoxy and two 3-amino-2,3,6-trideoxy sugars with orthogonal protecting groups were synthesized in 11–32 % overall yields in 74–131.5 minutes of total reaction time. Several of the reactions were able to be concatenated into a continuous process, avoiding the need for chromatographic purification of intermediates. The modular nature of the experimental setup allowed for reaction streams to be split into different lines for the parallel synthesis of multiple donors. Further, the continuous flow processes were fully automated and described through the design of an open-source Python-controlled automation platform.

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.