17682-70-1

Usage

Uses

Used in Organic Synthesis:
Diacetone L-sorbose is used as a key intermediate in organic synthesis for various applications. Its unique structure allows it to be a versatile building block for the creation of complex organic molecules, which can be utilized in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Diacetone L-sorbose is used as a starting material for the synthesis of various drugs. Its ability to form complex molecules makes it a valuable asset in the development of new medications, potentially contributing to the treatment of various diseases and conditions.
Used in Chemical Industry:
Diacetone L-sorbose is also used in the chemical industry for the production of specialty chemicals and materials. Its unique properties enable it to be a crucial component in the synthesis of advanced materials with specific applications, such as in the fields of electronics, coatings, and adhesives.

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

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 
• 74342-16-8 1-O-benzyl-2,3:4,6-di-O-isopropylidene-α-L-sorbofuranose 
• 116912-28-8 1-O-(Phenylacetyl)-2,3:4,6-di-O-isopropyliden-β-L-sorbofuranose 
• 18467-77-1 dikegulac 
• 52508-19-7 (3aS,3bR,7aS,8aR)-2,2,5,5-Tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxine-8a-carboxylic acid (3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-8a-ylmethyl ester 
• 3568-49-8 α-L-sorbofuranose-β-L-sorbofuranose 1,2':2,1'-dianhydride 
• 945394-93-4 2-benzoyl-3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol 
• 945394-95-6 3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol 
• 945395-01-7 2-O-allyl-3-O-benzyl-N-(tert-butoxycarbonyl)-1,5-dideoxy-1,5-imino-4,6-O-(4-methoxybenzylidene)-D-glucitol 
• 945394-84-3 6-azido-6-deoxy-1-O-benzyl-2,3-O-isopropylidene-α-L-sorbofuranose 
• 945394-86-5 6-azido-6-deoxy-1-O-benzyl-α-L-sorbofuranose 

Relevant academic research and scientific papers

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.

Zaragozic acid: Unusual stereochemical dependence in anhydride formation of carbohydrate templates

As a part of study on zaragozic acid bicyclic core, unusual observations in anhydro-ring formation depending on the stereochemistry at C-6 of the carbohydrate templates have been described.

A Green and Sustainable Route to Carbohydrate Vinyl Ethers for Accessing Bioinspired Materials with a Unique Microspherical Morphology

Synthesizing chemicals and materials from renewable sources is one of the main aims of modern science. Carbohydrates represent excellent renewable natural raw materials that are ecofriendly, inexpensive, and biologically compatible. A green procedure has been developed for the vinylation of carbohydrates by using readily available calcium carbide. Various carbohydrates were utilized as starting materials, resulting in mono-, di-, and tetravinyl ethers in high to excellent yields (81–92 %). The synthesized biobased vinyl ethers were utilized as monomers in free radical and cationic polymerizations. A unique combination of a smooth surface and intrinsic microcompartments was achieved in the synthesized materials. Two types of biobased materials were prepared involving microspheres and intrinsic hollow compartments in polymers. Scanning electron microscopy with built-in ion beam cutting was applied to reveal the spatial hierarchical structures in 3D space.

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.

A carbohydrate-based approach for the total synthesis of sawaranospirolide C

A diastereoselective carbohydrate-based synthesis of the oxaspirolactone sawaranospirolide C was accomplished by utilizing one-pot cascade of acetonide deprotection/hemiacetal formation/spirolactonization as the key step.

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.

A carbohydrate-based synthesis of the C13-C22 fragment of amphidinolide X

A facile carbohydrate-based route was developed for the synthesis of the tetrahydrofuran (C13-C22) fragment of amphidinolide X. Starting from L-sorbose, the key reactions followed include the stereoselective synthesis of a quaternary center at C1, Barton-

Triphenylphosphine polymer-bound/iodine complex: A suitable reagent for the preparation of O-isopropylidene sugar derivatives

O-Isopropylidene derivatives of sugars are readily prepared by using the Lewis acid and dehydrating agent triphenylphosphine polymer-bound/I2 complex. This new method is characterized by smooth, non-equilibrating reaction conditions and a very clean, simple work-up, making it particularly suitable for O-isopropylidenation of sugars under mild conditions and with low environmental impact. Georg Thieme Verlag Stuttgart.

Inhibition of the D-fructose transporter protein GLUT5 by fused-ring glyco-1,3-oxazolidin-2-thiones and -oxazolidin-2-ones

The glucose transporter 5 (GLUT5) - a specific D-fructose transporter - belongs to a family of facilitating sugar transporters recently enlarged by the human genome sequencing. Prompted by the need to develop specific photolabels of these isoforms, we have studied the interaction of conformationally locked D-fructose and L-sorbose derived 1,3-oxazolidin-2-thiones and 1,3-oxazolidin-2-ones to provide a rational basis for an interaction model. The inhibition properties of the D-fructose transporter GLUT5 by glyco-1,3-oxazolidin-2-thiones and glyco-1,3-oxazolidin-2-ones is now reported. In vitro, the fused-rings systems tested showed an efficient inhibition of GLUT5, thus bringing new insights on the interaction of D-fructose with GLUT5.