42926-89-6

Usage

Class

Glucopyranose derivatives

Explanation

1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose belongs to the class of glucopyranose derivatives, which are compounds derived from α-D-glucose.

Explanation

The compound is a derivative of α-D-glucose, a monosaccharide that serves as the parent molecule for this specific compound.

Explanation

The isopropylidene group is a chemical modification that is attached to the 1 and 2 positions of the glucose molecule, contributing to the compound's structure and properties.

Explanation

The benzyl group is another chemical modification attached to the 3 position of the glucose molecule, further defining the compound's structure and properties.

Explanation

1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose is used in organic chemistry for the synthesis of other carbohydrate derivatives and in medicinal chemistry for the development of potential drug candidates.

Explanation

The presence of the isopropylidene and benzyl groups in the compound allows for various chemical reactions and modifications, making it a valuable building block in organic synthesis.

Explanation

The compound is a modified version of α-D-glucofuranose, a five-membered ring form of α-D-glucose, with additional functional groups attached to specific positions on the ring.

Parent compound

α-D-glucose

Isopropylidene group

Attached at positions 1 and 2

Benzyl group

Attached at position 3

Applications

Organic chemistry and medicinal chemistry

Chemical reactivity

Enabled by isopropylidene and benzyl groups

Structure

Modified α-D-glucofuranose

Upstream product

• 72733-12-1 5.6-Di-O-benzoyl-3-O-benzyl-1.2-O-isopropyliden-β-L-idofuranose 
• 114475-14-8 3-O-benzyl-6-C-<(E)-6-O-benzyl-7-deoxy-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-heptopyranos-7-ylidene>-6-deoxy-1,2-O-isopropyledene-α-D-glucofuranose 
• 37776-17-3 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 
• 19877-13-5 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose 
• 1207730-45-7 3-O-benzyl-1,2-O-isopropylidene-6-O-(2,4,6-triisopropylbenzoyl)-β-L-idofuranose 
• 134198-40-6 6-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-α-D-glucofuranose 
• 37776-15-1 6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 50-99-7 D-glucose 
• 582-52-5 1,2:5,6-diacetone-D-glucose 
• 84563-90-6 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-α-D-glucofuranose 
• 18006-25-2 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose diacetate 
• 100-39-0 benzyl bromide 
• 22331-19-7 3-O-benzyl-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose 

Downstream Products

• 101475-83-6 3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 175978-71-9 1,2,4,6-tetra-O-benzoyl-3-O-benzyl-β-L-idopyranose 
• 1439518-81-6 C₂₅H₂₆O₅S 
• 1439516-36-5 C₂₅H₂₉BrO₅S 
• 1439516-28-5 C₂₅H₂₇BrO₅S 
• 5531-09-9 3-O-benzyl-L-idopyranose 
• 92772-78-6 (5S)-3-O-benzyl-1,2-O-isopropylidene-5-(quinizarin-2-yl)-α-D-xylofuranose 
• 92758-19-5 (5S)-3-O-benzyl-5-(quinizarin-2-yl)-α-(β)-D-xylopyranose 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 23313-03-3 (R)-2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl 4-methylbenzenesulfonate 
• 23313-05-5 6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose 

Relevant academic research and scientific papers

Method for synthesizing release type xylose ester perfume for tobacco perfuming

A synthesis method of a release type xylose ester spice for flavoring tobacco is provided. The glucose is used as a raw material, the principle of esterifying carboxylic acid and alcohol to prepare ester is adopted, a common parent carboxylic acid which c

PURE HEPTASULFATED DISACCHARIDES HAVING IMPROVED ORAL BIOAVAILABILITY

Hypersulfated disaccharides with utility in asthma or asthma related disorders are disclosed. The heptasulfated disaccharides administered orally have comparable bioavailability to the intravenous administered dosage form.

METHOD FOR PREPARING 3-O-BENZYL-1,2-O-ISOPROPYLIDENE-A-L-FURAN IDOSE

Provided is a method for preparing 3-O-benzyl-1,2-O-isopropylidene-α-L-idofuranose, which comprises: (1) protecting hydroxyl of 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (III) by benzoyl and methylsulfonyl to obtain 6-O-benzoyl-3-O-benzyl-1,2-O-is

METHOD FOR PREPARING 3-O-BENZYL-1,2-O-ISOPROPYLIDENE- -L-FURAN IDOSE

Provided is a method for preparing 3-O-benzyl-1,2-O-isopropylidene-α-L-idofuranose, which comprises: (1) protecting hydroxyl of 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (III) by benzoyl and methylsulfonyl to obtain 6-O-benzoyl-3-O-benzyl-1,2-O-is

Design and synthesis of carbohydrate based medium sized sulfur containing benzannulated macrocycles: Applications of Sonogashira and Heck coupling

Palladium catalyzed intramolecular Sonogashira and Heck coupling reactions have been applied for diversity-oriented synthesis of sulfur containing carbohydrate based medium sized ring macrocycles. The process involves design and synthesis of building bloc

Synthesis of carbohydrate fused chiral macrocyclic benzolactones through Sonogashira reaction

Synthesis of 10-, 11- and 12-membered chiral benzolactones fused to furanose/pyranose sugars has been achieved in good to excellent yields using an intramolecular Sonogashira reaction. Positions 1-2, 3-5, 3-6 and 5-6 of sugar were utilized for the constru

Environment friendly chemoselective deprotection of acetonides and cleavage of acetals and ketals in aqueous medium without using any catalyst or organic solvent

Highly chemoselective environment friendly deprotection of acetonides and cleavage of acetals and ketones has been achieved by heating in aqueous medium without using any catalyst and organic solvent. Indian Academy of Sciences.

Useful methods for the synthesis of isopropylidenes and their chemoselective cleavage

A catalytic amount of phosphotungstic acid (PTA) has been found to be a very effective catalyst for isopropylidenation of 1,2-diols and their deprotection at room temperature. The ease of handling, cost and activity of the catalyst, good to excellent yields and chemoselectivity for deprotection are some of the highlights of the reported method.

Novel formal synthesis of stereospecifically C-6 deuterated d-glucose employing configurationally stable alkoxymethyllithiums

The synthesis and testing of configurational stability of chirally monodeuterated PMB- and THP-substituted oxymethyllithiums are described. Macroscopically they are configurationally stable up to -35 °C, the limit of their chemical stability, and microscopically even up to 0 °C. Furthermore, THP-protected oxy-[D1]methyllithium has been applied in the formal synthesis of (6R)-[6-D1]-d-glucose (four steps, 40% yield), an example of its use as a homochiral hydroxymethyl synthon.

The role of the C-3 substituent in the asymmetric dihydroxylation of hexo-5-enofuranosides

Asymmetric dihydroxylation of vinyl furanosides 1-6 by use of OsO4, AD-mix-α and β is described yielding the corresponding hexofuranose sugars. Vinyl furanosides 2 and 3, with an ester group at C-3, and vinyl manno furanoside 5 on asymmetric dihydroxylation with AD-mix α exhibited high R diastereoselectivity at C-5. Reversal in diastereoselectivity at C-5 was observed for the 3-deoxy vinyl furanoside 6 giving furanosaccharide 6S with the S configuration at C-5.