6619-04-1

Basic information

• Product Name: α-D-Glucopyranoside, Methyl 2-(acetylaMino)-2-deoxy-4,6-O-(phenylMethylene)-
• Synonyms: α-D-Glucopyranoside, Methyl 2-(acetylaMino)-2-deoxy-4,6-O-(phenylMethylene)-;Methyl 2-acetamido-2-deoxy-4,6-O-benzylidene-alpha-D-glucopyranoside;Methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside;NSC 75588;1-[4-hydroxy-3-trityloxy-5-(trityloxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS NO: 6619-04-1
• Molecular Formula: C₁₆H₂₁NO₆
• Molecular Weight: 323.34104
• Mol File: 6619-04-1.mol

Chemical Properties

• Boiling Point: 579.4°Cat760mmHg
• Flash Point: 304.2°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 2.9E-14mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: α-D-Glucopyranoside, Methyl 2-(acetylaMino)-2-deoxy-4,6-O-(phenylMethylene)-(CAS DataBase Reference)
• NIST Chemistry Reference: α-D-Glucopyranoside, Methyl 2-(acetylaMino)-2-deoxy-4,6-O-(phenylMethylene)-(6619-04-1)
• EPA Substance Registry System: α-D-Glucopyranoside, Methyl 2-(acetylaMino)-2-deoxy-4,6-O-(phenylMethylene)-(6619-04-1)

Safety Data

• Hazardous Substances Data: 6619-04-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
α-D-Glucopyranoside, Methyl 2-(acetylaMino)-2-deoxy-4,6-O-(phenylMethylene)is used as a building block for the synthesis of novel pharmaceuticals due to its potential to interact with biological targets. The presence of the acetylamino group may allow for hydrogen bonding and other interactions with enzymes or receptors, while the phenylmethylene group could provide steric and hydrophobic properties that are crucial for the compound's activity and selectivity.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, this compound serves as a valuable research tool for studying the effects of structural modifications on biological activity. The ability to modify the sugar moiety, amine, and aromatic groups provides a platform for exploring structure-activity relationships and optimizing the compound's pharmacological properties.
Used in Drug Delivery Systems:
α-D-Glucopyranoside, Methyl 2-(acetylaMino)-2-deoxy-4,6-O-(phenylMethylene)may be utilized in the design of drug delivery systems, where its sugar component could enhance solubility and bioavailability, while the amine and phenylmethylene groups could facilitate targeting and release mechanisms within the body.
Used in Bioactive Compound Synthesis:
α-D-Glucopyranoside, Methyl 2-(acetylaMino)-2-deoxy-4,6-O-(phenylMethylene)is used as a precursor in the synthesis of bioactive compounds, leveraging its unique structure to create new molecules with potential therapeutic effects. The versatility of its functional groups allows for the development of compounds that could target a variety of diseases and conditions.

InChI:InChI=1/C16H21NO6/c1-9(18)17-12-13(19)14-11(22-16(12)20-2)8-21-15(23-14)10-6-4-3-5-7-10/h3-7,11-16,19H,8H2,1-2H3,(H,17,18)

Upstream product

• 100-52-7 benzaldehyde 
• 3946-01-8 methyl N-acetyl-β-D-glucosaminide 
• 6082-04-8 methyl 2-acetylamido-2-deoxy-D-glucoside 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 66537-92-6 methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside 
• 128657-58-9 methyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 3055-46-7 methyl N-acetyl-D-glucosamine 
• 100638-83-3 methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O--α-D-glucopyranoside 
• 67-56-1 methanol 
• 6748-94-3 methyl-[O³-acetyl-2-acetylamino-O⁴,O⁶-((R)-benzylidene)-2-deoxy-α-D-altropyranoside] 
• 10036-64-3 N-acetyl-D-glucosamine 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 

Downstream Products

• 139760-27-3 Methyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 139760-23-9 Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 120489-36-3 methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-pivaloyl-α-D-glucopyranoside 
• 139894-28-3 methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(p-methoxybenzyl)-α-D-glucopyranoside 
• 69892-42-8 methyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 139760-36-4 Methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 139760-31-9 Methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 23193-39-7 methyl-[2-acetylamino-O³-benzoyl-O⁴,O⁶-((Ξ)-benzylidene)-2-deoxy-α-D-glucopyranoside] 
• 85193-92-6 methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 85193-94-8 methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-β-D-galactopyranosyl-α-D-glucopyranoside 
• 85193-93-7 methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranoside 
• 139760-20-6 Methyl 2-acetamido-2-deoxy-3-O-(p-methoxybenzyl)-α-D-glucopyranoside 
• 93414-79-0 methyl 2-acetamido-4-azido-2,4,6-trideoxy-3-O-(p-methoxybenzyl)-α-D-galactopyranoside 
• 93414-78-9 methyl 2-acetamido-2,6-dideoxy-3-O-(p-methoxybenzyl)4-O-methylsulfonyl-α-D-glucopyranoside 

Relevant articles and documents

Ultrasonication-Assisted Synthesis of a d-Glucosamine-Based β-CD Inclusion Complex and Its Application as an Aqueous Heterogeneous Organocatalytic System

For the first time, an inclusion complex has been crafted between a carbohydrate-based molecule and a β-cyclodextrin (CD) hydrophobic cavity for asymmetric catalytic applications. This novel d-glucosamine-based inclusion compound has been synthesized in h

New phosphine-imine and phosphine-amine ligands derived from D-gluco-, D-galacto- and D-allosamine in Pd-catalysed asymmetric allylic alkylation

New phosphine-imine and phosphine-amine chiral ligands which were easily prepared from D-gluco-, D-galacto- and D-allosamine furnished a high level of enantiomeric excess (up to 99%) in the Pd(0)-catalysed asymmetric allylic alkylation of racemic 1,3-diphenyl-2-propenyl acetate with malonates.

Ring-Opening Reactions of the N-4-Nosyl Hough-Richardson Aziridine with Nitrogen Nucleophiles

Dinosylated α-d-glucopyranoside was directly transformed into α-d-altropyranosides via in situ formed N-4-nosyl Hough-Richardson aziridine with nitrogen nucleophiles under mild conditions in fair to excellent yields. The scope of the aziridine ring-opening reaction was substantially broadened contrary to the conventional methods introducing solely the azide anion at high temperatures. If necessary, the N-4-nosyl Hough-Richardson aziridine can be isolated by filtration in a very good yield and high purity.

Sugar derived alkamine catalytic imine reduction method

The invention discloses a method used for catalytic reduction of imine with saccharide-derivatized amino alcohol. According to the method, imine is taken as a substrate. The method comprises following steps: 1) imine and saccharide-derivatized amino alcohol are dissolved in an organic solvent I, wherein molar ratio of imine to saccharide-derivatized amino alcohol ranges from 100:1-20; 2) trichlorosilane with 1.5 to 5 times equivalent weights is added into a solution obtained via step 1) dropwise, an obtained mixture is stirred and reacted for 12 to 36h at a temperature of -20 to 40 DEG C, and a saturated sodium bicarbonate solution is used for quenching; 3) a material obtained via step 2) is extracted with an organic solvent II, and is subjected to column chromatography isolation so as to obtain amine compounds.

D-Glucosamine as a novel chiral auxiliary for the stereoselective synthesis of P-stereogenic phosphine oxides

D-Glucosamine was successfully employed as a chiral auxiliary for the enantioselective synthesis of phosphine oxides. The influence of the anomeric position was also investigated and revealed the excellent ability of the α-anomer to perform this transform

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The syntheses of methyl 2,3-diamino-4,6-O-benzylidene-2,3-dideoxy-α-d-hexopyranosides of glucose, mannose, gulose, and talose and methyl 2-amino-4,6-benzylidene-2,3-dideoxy-3-tosylamido-α-d-glucopyranoside are exhaustively presented, as well as their application as ligands in half-sandwich ruthenium(II), rhodium(III), and iridium(III) complexes. The complex formation occurs highly diastereoselectively, creating a stereogenic metal center. The molecular structures of the ligands and their complexes were investigated by X-ray structure analysis, NMR spectroscopy, polarimetry, and DFT methods. The diamino monosaccharide complexes have been subjected to antitumor activity studies. In vitro tests of a few ruthenium complexes against different cancer cell types showed antiproliferative activities 4-10 times lower than that of cisplatin.

3- and 4-uloses derived from N-acetyl- D -glucosamine: A unique pair of complementary organocatalysts for asymmetric epoxidation of alkenes

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2,4,6-Trichloro-1,3,5-triazine (TCT) mediated one-pot sequential functionalisation of glycosides for the generation of orthogonally protected monosaccharide building blocks

Orthogonally protected monosaccharide building blocks have been prepared using TCT in a one-pot multicomponent transformation. The process involves successive steps of arylidene acetalation, esterification and regioselective reductive acetal cleavage. High regioselectivity, scope for using a broad range of substrates, functional group tolerance, mild reaction conditions, easy handling process and wide application range are a few advantages of the current process.

Glucosamine-based primary amines as organocatalysts for the asymmetric aldol reaction

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Carbohydrate-based low molecular weight gelators are an interesting class of molecules with many potential applications. Previously, we have found that certain esters and carbamates of 4,6-O-benzylidene-α-d-methyl- glucopyranoside are low molecular weight