17682-70-1

Basic information

• Product Name: Diacetone L-sorbose
• Synonyms: 2,3:4,6-Di-O-isopropylidene-L-sorbose;Di-O-Isopropylidene-L-sorbose;NSC 23815;Sorbose Diacetonide;2,3:4,6-Di-O-isopropylidene-alpha-L-sorbofuranose min. 99%;alpha-L-Sorbose diacetonide;((3aS,3bR,7aS,8aS)-2,2,5,5-TetraMethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxin-8a-yl)Methanol;2,3,4,6-DI-O-ISOPROPYLIDENE-ALPHA-L-SORBOFURANOSE
• CAS NO: 17682-70-1
• Molecular Formula: C₁₂H₂₀O₆
• Molecular Weight: 260.28
• Product Categories: chiral;13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 17682-70-1.mol
• Article Data: 18

Chemical Properties

• Melting Point: 55-65°C
• Boiling Point: 329.3 °C at 760 mmHg
• Flash Point: 153 °C
• Appearance: White to Off-white/Powder
• Density: 1.181 g/cm³
• Vapor Pressure: 1.32E-05mmHg at 25°C
• Refractive Index: 1.467
• Storage Temp.: ?20°C
• Solubility: Acetone, Dichloromethane
• PKA: 14.66±0.10(Predicted)
• CAS DataBase Reference: Diacetone L-sorbose(CAS DataBase Reference)
• NIST Chemistry Reference: Diacetone L-sorbose(17682-70-1)
• EPA Substance Registry System: Diacetone L-sorbose(17682-70-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 17682-70-1(Hazardous Substances Data)

Usage

Chemical Properties

White Crytalline Solid

Uses

2,3:4,6-Di-O-isopropylidene-α-L-sorbofuranose (cas# 17682-70-1) is a compound useful in organic synthesis.

InChI:InChI=1/C12H20O6/c1-10(2)14-5-7-8(16-10)9-12(6-13,15-7)18-11(3,4)17-9/h7-9,13H,5-6H2,1-4H3

Upstream product

• 87-79-6 L-sorbose 
• 67-64-1 acetone 
• 7270-77-1 L-sorbopyranose 
• 7758-99-8 copper(II) sulfate 
• 7664-93-9 sulfuric acid 
• 35673-97-3 L-sorbose 
• 36468-68-5 L-sorbofuranose 
• 52507-90-1 methyl 2,3:4,6-di-O-isopropylidene-α-L-xylo-2-hexulofuranosonate 
• 18467-77-1 dikegulac 
• 116912-28-8 1-O-(Phenylacetyl)-2,3:4,6-di-O-isopropyliden-β-L-sorbofuranose 

Downstream Products

• 18609-97-7 O¹-benzoyl-O²,O³-isopropylidene-α-L-sorbofuranose 
• 2642-13-9 O²,O³;O⁴,O⁶-diisopropylidene-O¹-(toluene-4-sulfonyl)-α-L-sorbofuranose 
• 17682-71-2 2,3-O-isopropylidene-α-L-sorbofuranose 
• 85973-55-3 O¹-(toluene-4-sulfonyl)-L-sorbose 
• 74342-16-8 1-O-benzyl-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose 
• 1462919-42-1 1-O-p-methoxybenzyl-2,3-O-isopropylidene-α-L-sorbofuranose 
• 1462919-39-6 1-O-p-methoxybenzyl-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose 
• 58794-59-5 1-O-acetyl-2,3-O-isopropylidene-α-L-sorbofuranose 
• 1374552-67-6 (2R,3S,4S,5S)-2-allyl-4-(benzyloxy)-5-(benzyloxymethyl)-2-methyltetrahydrofuran-3-ol 

Relevant articles and documents

Synthesis of a constrained polyfunctional bicyclic iminocyclitol scaffold from l-sorbose via a tandem sequence including stereoselective intramolecular Huisgen cycloaddition

The synthesis of a functionalized (azido, amino, and hydroxy) 8-oxa-3-azabicyclo[3.2.1]octane framework and its conversion into a protected sugar amino acid and a tricyclic framework is described. The sequence includes a one-pot Huisgen 1,3-dipolar cycloaddition, with decomposition to an aziridine and subsequent ring opening by azide. The stereoselectivity observed in the Huisgen cycloaddition reaction is attributed to minimization of allylic strain.

CHEMICAL REACTION MECHANISM IN ACETONATION OF L-SORBOSE

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L-sorbose acetonation catalyzed by heteropolyacids

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2,3:4,6-Di-O-isopropyl-idene - L-sorbofuran-ose and 2,3-O-isopropyl-idene - L-sorbofuran-ose

In the title compounds, C12H20O6, (I), and C9H16O6, (II), the five-membered furan-ose ring adopts a 4 T 3 conformation and the five-membered 1,3-dioxolane ring adopts an E 3 conformation. The six-membered 1,3-dioxane ring in (I) adopts an almost ideal O C 3 conformation. The hydrogen-bonding patterns for these compounds differ substanti-ally: (I) features just one intra-molecular O - H...O hydrogen bond [O...O = 2.933 (3) A], whereas (II) exhibits, apart from the corresponding intra-molecular O - H...O hydrogen bond [O...O = 2.7638 (13) A], two inter-molecular bonds of this type [O...O = 2.7708 (13) and 2.7730 (12) A]. This study illustrates both the similarity between the con-formations of furan-ose, 1,3-dioxolane and 1,3-di-oxane rings in analogous isopropyl-idene-substituted carbohydrate structures and the only negligible influence of the presence of a 1,3-dioxane ring on the conformations of furan-ose and 1,3-dioxolane rings. In addition, in comparison with reported analogs, replacement of the -CH2OH group at the C1-furan-ose position by another group can considerably affect the conformation of the 1,3-dioxolane ring.

Composition with a polymer and an oxidation-catalyst

The present invention relates to a polymer composition with an increased rate of oxygen-uptake by the presence of an oxidation catalyst. The invention further relates to a process to increase the rate of oxygen-uptake by a polymer composition. The invention also relates to a process to increase the oxo-biodegradability of a polymer composition and to the use of such a composition for the preparation of a product having a controlled lifetime. The invention further relates to a process to increase the rate of oxygen-scavenging in a composition containing a carbon-containing polymer, the composition obtained by this method and its use in the preparation of an oxygen-scavenging product. The present invention further relates to objects containing an oxygen scavenging layer containing such a composition.