97-30-3

Basic information

• Product Name: alpha-D-Methylglucoside
• Synonyms: METHYL-ALPHA-D-GLUCOPYRANOSE;METHYL ALPHA-D-GLUCOPYRANOSIDE;METHYL ALPHA-D-GLUCOSIDE;METHYL A-D-GLUCOPYRANOSIDE;A-D-METHYLGLUCOSIDE;ALPHA-D-METHYLGLUCOSIDE;ALPHA-METHYLGLUCOSIDE;ALPHA-METHYL-D(+)-GLUCOSIDE
• CAS NO: 97-30-3
• Molecular Formula: C7H14O6
• Molecular Weight: 194.18
• EINECS: 202-571-3
• Product Categories: 13C & 2H Sugars;Biochemistry;Glucose;Glycosides;Sugars;Dextrins、Sugar & Carbohydrates;Carbohydrates & Derivatives
• Mol File: 97-30-3.mol
• Article Data: 210

Chemical Properties

• Melting Point: 169-171 °C(lit.)
• Boiling Point: 200 °C (0.2 mmHg)
• Flash Point: 189.1 °C
• Appearance: White/Fine Crystalline Powder
• Density: 1,46 g/cm3
• Vapor Pressure: 1.15E-07mmHg at 25°C
• Refractive Index: 157.5 ° (C=10, H2O)
• Storage Temp.: Store at RT.
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: pKa (25°): 13.71
• Water Solubility: 108 g/100 mL (20 ºC)
• Sensitive: Hygroscopic
• Merck: 14,6080
• BRN: 81568
• CAS DataBase Reference: alpha-D-Methylglucoside(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-D-Methylglucoside(97-30-3)
• EPA Substance Registry System: alpha-D-Methylglucoside(97-30-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 97-30-3(Hazardous Substances Data)

Usage

Chemical Properties

White Powder

Uses

Different sources of media describe the Uses of 97-30-3 differently. You can refer to the following data:
1. manufacture of reconstituted and upgraded drying oils; tall oil esters and varnishes; fatty acid esters; plasticizers; nonionic surface active agents; fast and hard drying alkyd resins, and so-called plasticizing alkyds. In making glucoside hydroxypropyl ethers for polyurethan foam production.
2. Methyl alpha-D-glucopyranoside is a biochemical used to vary echo decay times in a study that assessed the effects of cryoprotection on the structure and activity of p21ras. It is also used in a study to investigate saccharide-mediated protection of chaotropic-induced deactivation of concanavalin A.

Definition

ChEBI: An alpha-D-glucopyranoside having a methyl substituent at the anomeric position.

Flammability and Explosibility

Notclassified

Purification Methods

Crystallise methyl -D-glucoside from MeOH or EtOH. Its solubility in H2O is 10%. [Ferrier et al. Carbohydr Research 27 55,59 1973, Beilstein 17/7 V 13.]

InChI:InChI=1/C7H13O6/c1-12-6-5(10)4(9)3(2-8)13-7(6)11/h3-10H,2H2,1H3/q-1/t3-,4-,5+,6-,7+/m1/s1

Upstream product

• 67-56-1 methanol 
• 50-99-7 D-glucose 
• 6936-67-0 D-Glucose-dibenzyldithioacetal 
• 186581-53-3 diazomethane 
• 7045-43-4 α-anomer of trideca-O-methylpedunculagin 
• 2280-44-6 D-Glucose 
• 55908-11-7 methyl α-D-xylo-hexopyranosid-4-ulose 
• 55881-04-4 methyl 2-O-methanesulfonyl-α-D-glucopyranoside 
• 113963-39-6 7-O-methylwogonin 5-β-D-glucopyranoside 
• 113963-37-4 andrographidine A 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 709-50-2 methyl beta-D-glucopyranoside 
• 1464-44-4 phenyl-β-D-glucopyranoside 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 109097-22-5 methyl O⁴,O⁶-(4-chloro-phenylboranediyl)-α-D-glucopyranoside 
• 109097-21-4 methyl O⁴,O⁶-(3-nitro-phenylboranediyl)-α-D-glucopyranoside 
• 4056-12-6 methyl 4,6-O-(phenylborylene)-α-D-glucopyranoside 
• 24904-92-5 Acetic acid (2R,3R,4S,5R,6S)-3,4,5,6-tetramethoxy-tetrahydro-pyran-2-ylmethyl ester 
• 24904-97-0 2-O-acetyl-3,4,6-tri-O-methyl-α-D-glucopyranoside 
• 24951-71-1 methyl 4-O-acetyl-2,3,6-tri-O-methyl-α-D-glucopyranoside 
• 24904-95-8 methyl 3-O-acetyl-2,4,6-tri-O-methyl-α-glucopyranoside 
• 605-81-2 methyl 2,3,4,6-tetra-O-methyl-α-D-glucopyranoside 
• 35939-72-1 Methyl-2,4,6-tri-O-methyl-α-D-glucopyranosid 
• 10227-29-9 methyl 2,3-di-O-methyl-α-D-glucopyranoside 
• 28954-20-3 methyl-2,4-di-O-methyl-α-D-glucopyranoside 
• 7225-55-0 methyl 2,6-di-O-methyl-α-D-glucopyranoside 
• 23262-69-3 methyl 3,4-di-O-methyl-α-D-glucopyranoside 
• 23262-68-2 methyl 4,6-di-O-methyl-α-D-glucopyranoside 

Relevant articles and documents

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Access to septanoside diacetals from methyl α-D-glucopyranoside

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A simple method for detritylation of carbohydrate derivatives

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Loss of C-5 hydrogen during conversion of d-glucuronic acid into methyl α-d-glucopyranoside

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SELECTIVE VALORIZATION OF BIOMASS SUGARS

Disclosed are methods of forming an epimer or a dehydrated isomer of a pyranose monosaccharide or a pyranose saccharide residue in an oligosaccharide or a glycoside.

Carbon glycoside glycosylated tetravalent platinum compound as well as synthesis method and application thereof

The invention provides a carbon glycoside glycosylated tetravalent platinum compound, a synthesis method and application thereof. R1 and R2 are independently C1-C4 lower alkanes, R3 is glucose, galactose, mannose and ribose, different sugars are used as raw materials, and a series of carbon glycoside glycosylated tetravalent platinum compounds are synthesized through protection and deprotection reaction and metallization reaction of the sugars. The synthesis method is simple, the used raw materials are cheap and easy to obtain, the glycosylated tetravalent platinum compound has the capacity of targeting glucose transporter protein and has potential application value in the field of cancer treatment, introduction of a C-glucosidic bond enables the series of compounds to have the capacity of resisting hydrolysis of beta-glucosidase, and the compound is expected to be applied to the field of oral antitumor drugs.

Acceleration and deceleration factors on the hydrolysis reaction of 4,6-O-benzylidene acetal group

The benzylidene acetal group is one of the most important protecting groups not only in carbohydrate chemistry but also in general organic chemistry. In the case of 4,6-O-benzylidene glycosides, we previously found that the stereochemistry at 4-position altered the reaction rate constant for hydrolysis of benzylidene acetal group. However, a detail of the acceleration or deceleration factor was still unclear. In this work, the hydrolysis reaction of benzylidene acetal group was analyzed using the Arrhenius and Eyring plot to obtain individual parameters for glucosides (Glc), mannosides (Man), and galactosides (Gal). The Arrhenius and Eyring plot indicated that the pre-exponential factor (A) and ΔS? were critical for the smallest reaction rate constant of Gal among nonacetylated substrates. On the other hand, both Ea/ΔH? and A/ΔS? were influential for the smallest reaction rate constant of Gal among diacetylated substrates. All parameters obtained suggested that the rate constant for hydrolysis reaction was regulated by protonation and hydration steps along with solvation. The obtained parameters support wide use of benzylidene acetal group as orthogonal protection of cis- and trans-fused bicyclic systems through the fast hydrolysis of the trans-fused benzylidene acetal group.