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

General Description

The chemical compound "(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, which is a cyclic ether. The compound contains 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 the fields of organic chemistry, medicinal chemistry, and materials science due to its unique structure and functional groups. It is important to handle and use this compound 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

• 74-83-9 methyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 67-56-1 methanol 
• 62327-60-0 phenyl 2,3,4,6-tetra-O-methyl-1-thio-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 
• 95690-54-3 5-Methoxy-7-((2S,3R,4R,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-2-[4-((2S,3R,4R,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-chromen-4-one 
• 95690-55-4 Acetic acid (2R,3R,4R,5R,6S)-3,4,5-trimethoxy-6-{5-methoxy-4-oxo-2-[4-((2S,3R,4R,5R,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-4H-chromen-7-yloxy}-tetrahydro-pyran-2-ylmethyl ester 
• 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 
• 57631-96-6 C₂₆H₄₂O₁₁ 
• 74-88-4 methyl iodide 
• 64656-69-5 benzyl O-α-D-glucopyranosyl-(1->4)-β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 604-68-2 α-D-glucopyranose peracetylate 
• 95753-49-4 C₅₀H₈₁NO₂₁ 

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 
• 81874-02-4 1,5-anhydro-2,3,4,6-tetra-O-methyl-D-glucitol 
• 154-58-5 1,5-anhydro-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.

Efficient and selective removal of methoxy protecting groups in carbohydrates

(Chemical Equation Presented) The selective removal from carbohydrate substrates of methoxy protecting groups next to hydroxy groups is reported. On treatment with Phl(OAc)2-I2, the methoxy group is transformed into an easily removable acetal. The mild conditions of this methodology are compatible with many functional groups, and good to excellent yields are usually achieved.