4613-62-1

Basic information

• Product Name: 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane
• Synonyms: 1-O,2-O:5-O,6-O-Bis(isopropylidene)-3-deoxy-α-D-ribo-hexofuranose;1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-allofuranose;1-O,2-O:5-O,6-O-Diisopropylidene-3-deoxy-α-D-glucofuranose;NSC 59397;a-D-ribo-Hexofuranose, 3-deoxy-1,2:5,6-bis-O-(1-Methylethylidene)-;1,2:5,6-Di-O-Isopropylidene-3-deoxy-D-ribo-hexofuranose;3-Deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose;1,2:5,6-Di-O-isopropylidene-3-deoxy-alpha-D-ribo-hexofuranose
• CAS NO: 4613-62-1
• Molecular Formula: C₁₂H₂₀O₅
• Molecular Weight: 244.2842
• Mol File: 4613-62-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 291°Cat760mmHg
• Flash Point: 112°C
• Appearance: /
• Density: 1.123g/cm³
• Vapor Pressure: 0.00348mmHg at 25°C
• Refractive Index: 1.461
• CAS DataBase Reference: 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane(4613-62-1)
• EPA Substance Registry System: 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,7-dimethyl-2,6,8-trioxabicyclo[3.3.0]octane(4613-62-1)

Safety Data

• Hazardous Substances Data: 4613-62-1(Hazardous Substances Data)

Usage

Uses

An intermediate for 3-Deoxy-D-glucose.

InChI:InChI=1/C12H20O5/c1-11(2)13-6-9(16-11)7-5-8-10(14-7)17-12(3,4)15-8/h7-10H,5-6H2,1-4H3

Upstream product

• 617-86-7 triethylsilane 
• 130534-83-7 1,2:5,6-di-O-isopropylidene-3-O-(4-fluorophenoxy)thionocarbonyl-α-D-glucofuranose 
• 6027-62-9 3-deoxy-3-iodo-1,2:5,6-di-O-isopropylidene-α-D-allofuranose 
• 31818-51-6 Diethyl-thiocarbamic acid O-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester 
• 79233-85-5 O-[1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl] 1H-imidazole-1-carbothioate 
• 16667-96-2 Dithiocarbonic acid O-[(3aR,5S,6S,6aR)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester S-methyl ester 
• 107-13-1 acrylonitrile 
• 19189-62-9 O-((3aR,6S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl) O-phenylcarbonothioate 
• 16667-96-2 1,2,5,6-di-O-isopropylidene-α-D-glucofuranose-3-O-(S-methylxanthate) 
• 55951-93-4 1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose 
• 94-36-0 dibenzoyl peroxide 

Downstream Products

• 4005-46-3 3-deoxy-1,2-O-isopropylidene-D-glucose 
• 4005-35-0 3-Desoxy-D-galaktose 
• 23655-60-9 3-deoxy-1,2:5,6-tetra-O-acetyl-β-D-glucofuranose 
• 23655-60-9 3-deoxy-1,2:5,6-tetra-O-acetyl-α-D-glucofuranose 
• 4105-29-7 [(3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate 
• 499-87-6 3-deoxy-D-ribo-hexono-1,4-lactone 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 108380-28-5 (S)-5-(2-(benzyloxy)ethyl)dihydrofuran-2(3H)-one 
• 169392-07-8 [(1S,2R)-2-Benzyloxy-1-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-ylmethyl)-propoxy]-tert-butyl-dimethyl-silane 
• 169392-05-6 (4S,6R)-4-((R)-1-Benzyloxy-ethyl)-6-(bis-ethylsulfanyl-methyl)-2,2-dimethyl-[1,3]dioxane 
• 169392-06-7 2-[(4R,6S)-6-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propan-2-ol 
• 169392-04-5 (3aR,5S,6aR)-5-((R)-1-Benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 180469-63-0 5-F_2t-isoprostane 
• 223574-25-2 (E)-(4R,6S,7S)-8-(tert-Butyl-diphenyl-silanyloxy)-4,6-dihydroxy-7-iodo-oct-2-enoic acid methyl ester 

Relevant articles and documents

Novel Position-Specific 18O/16O Measurement of Carbohydrates. I. O-3 of Glucose and Confirmation of 18O/16O Heterogeneity at Natural Abundance Levels in Glucose from Starch in a C4 Plant

The 18O/16O ratio at both molecular and positional levels in the carbohydrates of higher plants is a reliable proxy for the plant growth environment, and a potential indicator of the plant photosynthetic carbon assimilation mode, and its physiological, biochemical and metabolic status. The lack of exploitable nuclear resonance in 18O and 16O and the extremely low 17O abundance make the NMR-based PSIA (position-specific isotopic analysis) a significant challenge. In this Article, an alternative three-step wet chemistry based method for accessing the 18O/16O of glucose O-3 is presented. The O atoms (OH groups) at positions 1, 2, 5, and 6 were first protected by acetonation (converting glucose to 1,2;5,6-di-O-isopropylidene-glucofuranose). The protected glucose was then esterified at O-3 by thionoformylation. Subsequent Barton-McCombie deoxygenation quantitatively removed the O-3 from the protected sugar. Mass balance was then applied to calculate the 18O/16O of O-3 using the isotopic values of the protected sugar before and after the deoxygenation step. The method is innovative in that (i) isolation and purification of individual compounds for 18O by EA/Pyrolysis/IRMS analysis is unnecessary as the reaction mixture can be analyzed on a GC/Pyrolysis/IRMS; (ii) sample quantity is dramatically reduced; and (iii) the approach to access the O-3 isotopic signal can be easily expanded to other positions within glucose and other sugars. It was shown that O-3 is enriched by 12 mUr relative to the molecular average (O-2-O-6) for a glucose of C4 photosynthetic origin. We highlighted the potential applications of the intramolecular O isotopic heterogeneity of glucose this method revealed.

Efficient Large-Scale Radical Deoxygenation in Alcoholic Solvents Using Sodium Hypophosphite and a Phase-Transfer Agent: Application to Erythromycins

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The invention of radical reactions. Part XXIX. Radical mono- and dideoxygenations with silanes

Thionocarbonates and xanthates of primary and secondary alcohols, as well as bis-xanthates of vic-diols are readily deoxygenated to the corresponding hydrocarbons or olefins with phenylsilane, triphenylsilane, and triethylsilane in good yield.