253328-56-2

Basic information

• Product Name: 1,2-O-Isopropylidene-α-D-glucofuranose
• Synonyms: (5ξ)-1,2-O-(1-Methylethylidene)-α-D-xylo-hexofuranose
• CAS NO: 253328-56-2
• Molecular Formula: C₉H₁₆O₆
• Molecular Weight: 220.21974
• Product Categories: Carbohydrates & Derivatives
• Mol File: 253328-56-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 156-158°C
• Boiling Point: 422.4±40.0 °C(Predicted)
• Appearance: /
• Density: 1.358±0.06 g/cm3(Predicted)
• PKA: 13.19±0.60(Predicted)
• CAS DataBase Reference: 1,2-O-Isopropylidene-α-D-glucofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-Isopropylidene-α-D-glucofuranose(253328-56-2)
• EPA Substance Registry System: 1,2-O-Isopropylidene-α-D-glucofuranose(253328-56-2)

Safety Data

• Hazardous Substances Data: 253328-56-2(Hazardous Substances Data)

Usage

Description

1,2-O-Isopropylidene-α-D-glucofuranose is a white crystalline solid that serves as a valuable compound in the field of organic synthesis. It is characterized by its unique chemical structure, which makes it a versatile building block for the creation of various complex organic molecules.

Uses

Used in Organic Synthesis:
1,2-O-Isopropylidene-α-D-glucofuranose is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows it to be easily modified and incorporated into a wide range of molecules, making it a valuable asset in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2-O-Isopropylidene-α-D-glucofuranose is used as a key component in the development of novel drug candidates. Its ability to be modified and incorporated into complex molecular structures makes it an ideal starting material for the design and synthesis of new therapeutic agents.
Used in Agrochemical Industry:
1,2-O-Isopropylidene-α-D-glucofuranose is also utilized in the agrochemical industry for the synthesis of bioactive compounds with potential applications in pest control, crop protection, and other agricultural settings. Its versatility in organic synthesis enables the development of innovative and effective solutions to address various challenges in agriculture.
Used in Specialty Chemicals:
In the specialty chemicals sector, 1,2-O-Isopropylidene-α-D-glucofuranose is employed as a building block for the synthesis of various high-value compounds with specific applications in industries such as cosmetics, fragrances, and flavors. Its unique properties and reactivity make it an essential component in the development of these specialty products.

Upstream product

• 67-64-1 acetone 
• 28069-98-9 Acetic acid (3aR,5R,6S,6aR)-5-(1,2-diacetoxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 7284-07-3 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-eno-furanose 
• 19684-32-3 1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose 
• 67-56-1 methanol 
• 113544-32-4 (S)-3-O-(2-(2-fluoro-4-biphenyl)propionyl)-1,2-O-isopropylidene-α-D-glucofuranose 
• 113544-32-4 (R)-3-O-(2-(2-fluoro-4-biphenyl)propionyl)-1,2-O-isopropylidene-α-D-glucofuranose 
• 113544-34-6 (S)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,5R,6S,6aR)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 113544-34-6 (R)-2-(6-Methoxy-naphthalen-2-yl)-propionic acid (3aR,5R,6S,6aR)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 113544-36-8 (S)-2-(4-Isobutyl-phenyl)-propionic acid (3aR,5R,6S,6aR)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 113544-36-8 (R)-2-(4-Isobutyl-phenyl)-propionic acid (3aR,5R,6S,6aR)-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 

Downstream Products

• 10310-32-4 tribenoside 
• 53167-11-6 1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 
• 1310685-34-7 (E)-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose-5-O-benzyloxime 
• 89157-91-5 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 29364-56-5 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 28069-98-9 Acetic acid (3aR,6S,6aR)-5-((R)-1,2-diacetoxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 74708-51-3 3,5-O-(S)-benzylidene-1,2-O-isopropylidene-α-D-glucofuranose 
• 55169-72-7 3',5'-di-O-methyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 5488-90-4 5'-O-methyl-1,2-O-isopropylidene-α-D-glucofuranose 

Relevant articles and documents

Sulfonic Acid Functionalized Ordered Mesoporous Silica and their Application as Highly Efficient and Selective Heterogeneous Catalysts in the Formation of 1,2-Monoacetone-D-glucose

A series of sulfonic acid functionalized ordered mesoporous silica (OMS), designated as RSO3H-OMS (R=alkyl or aryl; OMS=MCM-41, IITM-56 or SBA-15), were prepared by post-synthesis grafting method. These catalysts, in general, exhibit strong acidic sites and, therefore, yield diacetone-D-glucose as main product in the D-glucose acetonation reaction. On the other hand, the functionalized catalyst can also be tuned in such a way to generate significant amount of weak-to-moderate acidic sites, which are in turn responsible for the formation of 1,2-monoacetone-D-glucose, hitherto not reported so far. These functionalized materials also show promise as they are water tolerant catalyst as well as exhibit varying acidic strengths, which allow greater flexibility for the desired product. In addition, the uniform mesopores with high surface area permit bulkier molecules to enter the active sites, thus the catalyst offers larger pliability in terms of yield and reusability. We report here, for the first time, RSO3H-SBA-15, with sizable amount of weak-to-moderate acidic sites, as a robust heterogeneous catalyst for the formation of the targeted molecule, 1,2-monoacetone-D-glucose.

Indium(III) triflate: A highly efficient catalyst for reactions of sugars

Indium(III) trifluoromethanesulfonate has been found to be extremely efficient in catalyzing acyl transfer reactions of various carbohydrates and their derivatives. Selective acetolyses of certain benzyl ethers/isopropylidene acetals of sugars have been possible using In(OTf)3 in Ac2O (neat). Reaction of the per-O-acetate of 2-deoxy-2-phthalimido-D-glucose with benzyl mercaptan in the presence of In(OTf)3 led to the formation of the corresponding thioglycoside in high yield. Facile formation and hydrolysis of the isopropylidene and benzylidene acetals of various carbohydrates have also been achieved very efficiently in the presence of In(OTf)3. The results show great promise for In(OTf)3 in synthetic carbohydrate chemistry.

Nafion-H mediated selective deprotection of terminal isopropylidene acetals and trityl ethers. Application in the synthesis of a substituted piperidone

A facile chemoselective hydrolysis of terminal isopropylidene acetals has been achieved in good to excellent yields within 2-4 h using Nafion-H in methanol at ambient temperature. This procedure has been employed to synthesize a substituted piperidone der