3149-65-3

Basic information

• Product Name: (2R,5R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane
• Synonyms: (2R,5R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane;methyl 2,3,4,6-tetra-O-methylglucopyranoside;1-O,2-O,3-O,4-O,6-O-Pentamethyl-β-D-glucopyranose;Methyl 2-O,3-O,4-O,6-O-tetramethyl-β-D-glucopyranoside;.beta.-D-Glucopyranoside, methyl 2,3,4,6-tetra-o-methyl-;Glucopyranoside, methyl tetra-o-methyl-, .beta.-D-;Methyl tetra-o-methyl-.beta.-D-glucoside;Nsc226830
• CAS NO: 3149-65-3
• Molecular Formula: C₁₁H₂₂O₆
• Molecular Weight: 250.29
• Mol File: 3149-65-3.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 305.2°C at 760 mmHg
• Flash Point: 117.5°C
• Appearance: /
• Density: 1.07g/cm³
• Vapor Pressure: 0.00151mmHg at 25°C
• Refractive Index: 1.44
• CAS DataBase Reference: (2R,5R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane(3149-65-3)
• EPA Substance Registry System: (2R,5R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane(3149-65-3)

Safety Data

• Hazardous Substances Data: 3149-65-3(Hazardous Substances Data)

Usage

Description

(2R,5R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane is a complex organic compound with a molecular formula of C11H22O6. It is a derivative of oxane, a cyclic ether, featuring four methoxy groups and one methoxymethyl group attached to the oxane ring. (2R,5R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane may have potential applications in various fields such as organic chemistry, medicinal chemistry, and materials science due to its unique structure and functional groups.

Uses

Used in Organic Chemistry:
(2R,5R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane is used as a building block for the synthesis of more complex organic molecules, taking advantage of its unique structure and functional groups.
Used in Medicinal Chemistry:
(2R,5R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane is used as a potential pharmaceutical candidate for the development of new drugs, given its unique structure and functional groups that can be utilized in medicinal chemistry.
Used in Materials Science:
(2R,5R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane is used as a component in the development of new materials with specific properties, such as polymers or other materials with tailored characteristics.
It is important to handle and use (2R,5R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane with care, following all necessary safety precautions and guidelines.

InChI:InChI=1/C11H22O6/c1-12-6-7-8(13-2)9(14-3)10(15-4)11(16-5)17-7/h7-11H,6H2,1-5H3/t7?,8-,9?,10?,11-/m1/s1

Upstream product

• 67-56-1 methanol 
• 492-62-6 alpha-D-glucopyranose 
• 74-88-4 methyl iodide 
• 118525-44-3 C₄₅H₆₈O₁₅ 
• 95753-49-4 C₅₀H₈₁NO₂₁ 
• 74-83-9 methyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 
• 2280-44-6 D-Glucose 
• 62327-60-0 phenyl 2,3,4,6-tetra-O-methyl-1-thio-β-D-glucopyranoside 
• 64656-69-5 benzyl O-α-D-glucopyranosyl-(1->4)-β-D-glucopyranoside 
• 57631-96-6 C₂₆H₄₂O₁₁ 
• 19146-24-8 methyl 2,3,6-tri-O-methyl-4-O-(2,3,4,6-tetra-O-methyl-α-D-glucopyranosyl)-β-D-glucopyranoside 
• 95690-50-9 7-Hydroxy-5-methoxy-2-[4-((2S,3R,4R,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-chromen-4-one 

Downstream Products

• 38791-30-9 ethyl 2,3,4,6-tetra-O-methyl-β-D-glucopyranoside 
• 605-81-2 methyl 2,3,4,6-tetra-O-methyl-α-D-glucopyranoside 
• 154-58-5 1,5-anhydro-D-glucitol 
• 81874-02-4 1,5-anhydro-2,3,4,6-tetra-O-methyl-D-glucitol 

Relevant articles and documents

Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity

Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.

Selective cleavage of methoxy protecting groups in carbohydrates

The selective cleavage of methoxy protecting groups next to hydroxy groups is achieved using a radical hydrogen abstraction reaction as the key step. Under the reaction conditions, the hydroxy group generates an alkoxyl radical that reacts with the sterically accessible adjacent methoxy group, which is transformed into an acetal. In the second step, the acetals are hydrolyzed to give alcohols or diols. A one-pot hydrogen abstraction-hydrolysis procedure was also developed. Good yields were usually achieved, and the mild conditions of this methodology were compatible with different functional groups and sensitive substrates such as carbohydrates.

Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry

(Chemical Equation Presented) Alkoxycarbenium ions have been generated and accumulated as "cation pools" by the low-temperature electrochemical oxidation of α-phenylthioethers. Although an unsuccessful attempt to accumulate glycosyl cations was made, a one-pot method for electrochemical glycosylation, which involves anodic oxidation of thioglycosides to generate glycosyl cation equivalents followed by their reactions with glycosyl acceptors, has been developed.