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

• 39524-38-4 2,3,4-tri-O-acetyl-6-deoxy-beta-L-mannopyranosyl bromide 
• 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 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 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 
• 53657-42-4 L-rhamnal 

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.

Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals

A novel synthetic route for highly substituted conjugated ketones has been developed utilizing glycals as starting materials. The two-step process combined the Heck reaction/Lewis acid promoted ring opening to afford the products in 33–80 % overall yields and with a high level of trans stereoselectivity. Since the products are essentially the aldols, this methodology may be employed in some cases as an alternative synthetic route to the typical aldol condensation. Densely substituted, selectively protected conjugated ketones are synthetically attractive structures which, in our case, proved to be biologically equally appealing. Namely, they showed activity against several cancer cell lines, such as HeLa, K562, MDA-MB-453, in some instances overperforming cisplatin used as a standard.